PeptidesFrontiers of Peptide Science

PeptidesFrontiers of Peptide Science

Proceedings of the Fifteenth American Peptide SymposiumJune 14-19, 1997, Nashville, Tennessee, U.S.A.

Edited by

James P. TamDepartment of Microbiology and Immunology,Vanderbilt University Medical School,Nashville, Tennessee, U.S.A.

and

Pravin T. P. KaumayaDepartments of Ob/Gyn, Medical Biochemistry and Microbiology andThe Comprehensive Cancer Center,The Ohio State University,Columbus, Ohio, U.S.A.

KLUWER ACADEMIC PUBLISHERS NEW YORK, BOSTON, DORDRECHT, LONDON, MOSCOW

62 X7923-5160 6

1999

Contents

Preface

Fifteenth American Peptide symposium Committees

Acknowledgments - Benefactors, Sponsors, Donors, and Contributors

The First Merrifield Award and Past Alan E. Pierce Awards

American Peptide Symposia

1997 Young Investigators Poster Competition Awards

American Peptide Society Travel Grant Recipients

Abbreviations

First Merrifield Award Lecture-Makineni Lecture

Fifty Years of My Protein SynthesisShumpei Sakakibara

Keynote Lecture

“The time has come,” the walrus said, “to talk of many things...” -Lewis 11Carroll, Through the Looking Glass

Ralph Hirschmann

Session I. Peptide Diversity/Chemical LibrariesNovel Concepts for the Synthesis of Cyclic Peptide Libraries

Lianshan Zhang and James P. Tam

Combinatorics, Peptide Mimetics, and CombizymesHyunsoo Han, Anthony M. Vandersteen, and Kim D. Janda

Peptides as Precursors in the Synthesis of Heterocyclic Positional ScanningCombinatorial Libraries

Jean-Philippe Meyer, John M. Ostresh, Adel Nefzi, Vince T. Hamashin,Christa C. Schoner, Marc A. Giulianotti, Amy L. Hannah, and Richard A.Houghten

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Expanding Molecular Diversity with Pseudopeptides and Macrotorials:Synthesis, Characterization and Biological Activities of MacrocyclicCombinatorial Libraries

Arno F. Spatola, Yvon Crozet, Peteris Romanovskis, and David Vogel

Solid Phase Synthesis of PeptidomimeticsJ.P. Mayer, D. Bankaitis-Davis, G. Beaton, K. Bjergarde, J.J. Gaudino,B.A. Goodman, C.J. Herrera, D.M. Lenz, G.S. Lewis, C.M. Tarlton,and J. Zhang

Determination of the Amino Acid Composition of the Bioactive Componentsin Peptide Libraries

Árpád Furka, Eugen Câmpian, Hans R. Tanner, and Hossain H. Saneii

Backbone Amide Linker (BAL) for Solid-Phase Synthesis of 2,5-Piperazinediones (DKP), Useful Scaffolds for Combinatorial Chemistry

Fernando Albericio, Montse del Fresno, Ariadna Frieden, Miriam Royo,Jordi Alsina, Knud J. Jensen, Steven A. Kates, and George Barany

Fluorescent Quenched Substrates for Protein Disulfide Isomerase (PDI)Defined By the Use of Disulfide Bridge Containing Libraries

J.C. Spetzler, V. Westphal, J.R. Winther, and M. Meldal

Solid Phase Synthesis of Cyclic Homodetic Peptide Libraries Utilizing aNovel Intraresin Chain Transfer

Michael L. Moore, Kenneth A. Newlander, Heidemarie Bryan, William M.Bryan, and William F. Huffman

Analysis of O-And N-Linked Glycopeptide Libraries by MALDI-TOF MS:Application in Solid Phase Assays of Carbohydrate-Binding-Proteins

Phaedria M. St.Hilaire, Morten Meldal, and Klaus Bock

Unsymmetrically Functionalized Polyamine Libraries by a Solid PhaseStrategy Starting from their Symmetrical Polyamine-Counterparts

Gerardo Byk, Marc Frederic, and Daniel Scherman

Development of DNA-Encoded Library Containing Backbone CyclicPeptides on Glass Beads

Anna Balanov, Eran Hadas, and Ilana Cohen

Introduction of Bulky Betidamino Acids in Thyrotropin Releasing Hormone(TRH)

Dean A. Kirby, Marvin C. Gershengorn, and Jean E. Rivier

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Combinatorial Libraries and Polyamines in the Battle against Third WorldTrypanosomesHelen K. Smith and Mark Bradley

Hybrid Resin for Synthesis and Screening of Synthetic Peptide LibrariesHoebert S. Hiemstra, Willemien E. Benckhuijsen, Wolfgang E. Rapp, andJan W. Drijfhout

Combinatorial Libraries: Equimolar Incorporation of Benzaldehyde Mixtures inReductive Alkylation Reactions

John M. Ostresh, Christa C. Schoner, Marc A. Giulianotti, Michael J.Kurth, Barbara Dörner, and Richard A. Houghten

Potential Cancer Vaccine: Anti-Idiotype Antibodies Developed from AntigenBinding Peptides Bind to Human Breast Cancer Antigen

John Mark Carter, Judy Singleton, Phoebe Strome, Cindy Coleman, andVernon Alvarez

Studying Receptor-Ligand Interactions Using Encoded Amino Acid ScanningJulio A. Camarero, Joanna Pavel, and Tom W. Muir

A Double-Bond-Containing Angiotensin and Its Derivatization into Linear vs.Branched Analogs

Kun-hwa Hsieh and Garland R. Marshall

Synthesis and Application of Tyrosine Kinase Substrate LibrariesSong Zheng, Richard Cummings, Rose Cubbon, Young-Whan Park,Patricia Cameron, Patrick Griffin, and Jeffrey Hermes

Encoding Schemes for Application with Polyethylene Glycol-Polystyrene Graft(PEG-PS) Supports in Solid-Phase Peptide and Small Molecule Synthesis

Steven A. Kates, Wade Hines, Michael A. Kelley, Paul Lynch, FernandoAlbericio, and George Barany

Use of Phage Display and Cellulose-Bound Peptide Libraries for theIdentification of Urea Herbicide Binding Peptides

Ulrich Hoffmüller, Christine Rottenberger, Günter Wellnhofer, LeodevicoL. Ilag, Jürgen Spindler, and Jens Schneider-Mergener

High Affinity Binding Peptides for PhosphataseStefan Vetter and Holger Schmid

Session II. De Novo Design of Peptides & ProteinsFive Axioms for Protein Engineering: Keys for Understanding ProteinStructure/Function?

Dan W. Urry

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Novel Collagen-Mimetic StructuresElizabeth A. Jefferson, and Murray Goodman

De Novo Design of Helical Coiled-Coils: the Effect on Stability of AminoAcid Substitution in the Hydrophobic Core

Kurt C. Wagschal, Brian Tripet, Pierre Lavigne, and Robert S. Hodges

Towards Full Mimics of Antibodies: A 37-aa Miniprotein with TwoIndependent Activities

Antonello Pessi, Elisabetta Bianchi, Jaques Neyton, Eugenia Drakopolou,and Claudio Vita

Optical Holographic Data Storage Using PeptidesRolf H. Berg, Palle H. Rasmussen, Soren Hvilsted, and P.S. Ramanujam

Developing Synthetic Hemoprotein Mimetics: Design, Synthesis andCharacterization of Heme-Peptide Conjugates

Angela Lombardi, Flavia Nastri, Luca D. D’Andrea, Ornella Maglio,Gabriella D’Auria, Carlo Pedone, and Vincenzo Pavone

A Novel Class of Calmodulin Mimetics: De Novo Designed Proteins inMolecular Recognition

Angela Lombardi, Giovanna Ghirlanda, Laura Zaccaro, VincenzoPavone, and William F. DeGrado

Non native Architectures in Protein Design: Four Helix Bundles as Locked-in Tertiary Fold

Marc Mathieu and Gabriele Tuchscherer

Synthesis and In Vivo Pharmacological Profile of Dimeric HOE 140Bradykinin antagonists

Muriel Amblard, Isabelle Daffix, Gilbert Bergé, Pierre Dodey, DidierPruneau, Jean-Luc Paquet, Pierre Bélichard, Jean-Michel Luccarini, andJean Martinez

Conformations and Use of Beta-Amino Acid ResiduesIsabella L. Karle

Modular Design of Synthetic Redox and Light-Absorbing ProteinsWolfgang Haehnel, Harald K. Rau, Heike Snigula, and Hugo Scheer

Synthesis of Semicaged Ruthenium(II) Complexes of a Branched PeptideContaining Three Bipyridine Ligands

Barney M. Bishop, Matthrew C. Foster, Richard W. Vachet, and BruceW. Erickson

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Design of New Tentoxin Analogues: Study of the ATP-Synthase CatalyticMechanism

Florine Cavelier, Christine Enjalbal, Jérôme Santolini, Francis

Novel Disubstituted Amino Acids for Peptide Secondary StructureControl

Christopher L. Wysong, Muna K. Thalji, Thad A. Labbe, and Robert P.Hammer

Design of Antimicrobial Peptides Based on Sequence Analogy andAmphipathicity

A. Tossi, C. Tarantino, N. Mitaritonna, G. Rocco, and D. Romeo

Synthesis and Structural Characterization of the Ligand Binding Site ofMacrophage Scavenger Receptor

Hironobu Hojo, Yoshiko Akamatsu, Yu Nakamura, Shunji Miki, KiyoshiYamauchi, and Masayoshi Kinoshita

Enantiomeric Structural Libraries of Unnatural Peptides Which Bind DNAand Alter Enzymatic Activity

L.M. Martin, B-H Hu, and C. Li

Interplay of Hydrophobic and Electrostatics in Peptide-bilayer InteractionsLi-Ping Liu and Charles M. Deber

An Investigation of Position 3 in Arginine Vasopressin (AVP)M. Manning, S. Stoev, L.L. Cheng, A. Olma, W.A. Klis, W.H. Sawyer,N.C. Wo, and W.Y. Chan

Design and Expression of Recombinant Rop Protein Analogs Which HaveMetal Binding Ability

Takahisa Nakai, Osamu Odawara, Takemune Yasuda, and Nobutaka Tani

Combination of Helix Peptides with Intercalator Anthracene for ReportingPeptide-DNA Interactions

Tsuyoshi Takahashi, Akihiko Ueno, and Hisakazu Mihara

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Haraux, Claude Sigalat, Jean Verducci, and François André

Investigation of conformational Properties of Calcium-binding Peptides inthe Cell Adhesion Molecules

Wei Yang and Jenny J. Yang

End Capping and Helix Stabilization in Short PeptidesHemender K. Reddy, and Krishnan P. Nambiar

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Macrotorials: Concept and Synthetic Examples Using PTH(1-34)Wanli Ma, Jeffrey A. Dodge, and Arno F. Spatola

Metal Ion-induced Folding of a De Novo Designed (-Helical Coiled-coilW.D. Kohn, C.M. Kay, and R.S. Hodges

to Transitions of Peptides Caused by Hydrophobic DefectsYuta Takahashi, Akihiko Ueno, and Hisakazu Mihara

A Natural Motif Approach to Protein Folding and Design Daniel J. Butcher, M.Anna Kowalska, Song Li, Zhaowen Luo, Simei Shan,Zhixian Lu, Stefan Niewiarowski, and Ziwei Huang

Engineering of a Cationic Coiled-Coil Protein Bearing RGD-Like Ligands onProline-II Helical Spacers

Harold D. Graham Jr., Deborah M. John, and Bruce W. Erickson

Conformational Comparison of Peptide Templates and Their FoldingEnhancements on TASP

Zhenwei Miao, Guangzhong Tu, Xiaojie Xu, Riqing Zhang, and YouqiTang

Use of a Potent and Selective Highly Constrained Peptide Agonist to DesignDe Novo an Equally Potent and Selective Non-Peptide Mimetic for theOpioid Receptor

Victor J. Hruby, Subo Liao, Mark D. Shenderovich, Josue Alfaro-Lopez,Keiko Hosohata, Peg Davis, Frank Porreca, and Henry I. Yamamura

Engineering of the Deltoid Protein: A Model for the Four Corners ofQuadrin, a Square Octamer from the Hepatitis delta Antigen

Matthew J. Saderholm, Gopal K. Balachandran, Stanley M. Lemon, andBruce W. Erickson

Engineering of Helical Oligoproline Redox Assemblies That UndergoPhotoinduced Electron Transfer

Cheryl A. Slate, Durwin R. Striplin, Robert A. Binstead, Thomas J. Meyer,and Bruce W. Erickson

The Use of 5-tert-Butylproline to Study Nucleation of Polyproline Type IConformation

Eric Beausoleil, and William D. Lubell

Structure-Activity Relationships in Cyclic -Sheet Antibacterial PeptidesLeslie H. Kondejewski, Masood Jelokhani-Niaraki, Robert E.W. Hancock,and Robert S. Hodges

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Chimeric TASP Molecules as BiosensorsLukas Scheibler, Pascal Dumy, Mila Bontcheva, Horst Vogel, andManfred Mutter

Topologies of Consolidated Ligands for the SRC Homology (SH)3 and SH2Domains of Abelson Protein-Tyrosine Kinase

Qinghong Xu, Jie Zhang, George Barany, and David Cowburn

Toward Design of a Triple Stranded Antiparallel -SheetHeather L. Schenck, and Samuel H. Gellman

Copper(II)-Induced Folding of Betabellin 15D, a Designed Beta-SheetProtein

Amareth Lim, Mathias Kroll, Yibing Yan, Matthew J. Saderholm,Alexander M. Makhov, Jack D. Griffith, and Bruce W. Erickson

Engineering of an Iron(II)-Braced Tripod Protein Containing Proline-IIHelical Legs

Bassam M. Nakhle, Tracie L. Vestal, Matthew J. Saderholm, and BruceW. Erickson

De Novo Design and Synthesis of a Heme-binding Four-helix TASP Capableof Light-induced Electron Transfer

Harald K. Rau, Niels de Jonge, and Wolfgang Haehnel

Inhibition of Nitric Oxide Synthase with Calmodulin Binding PeptidesKaren S. Gregson, Michael A. Marletta, and Henry I. Mosberg

Improved Peptides for Holographic Data StoragePalle H. Rasmussen, P.S. Ramanujam, Søren Hvilsted, and Rolf H. Berg

Session III. Peptide MimeticsStructure-Based De Novo Design and Discovery of Novel Peptidomimeticand Nonpeptide Antagonists of the (Src) SH2 Domain

K.S. Para, E.A. Lunney, M.S. Plummer, C.J. Stankovic, A. Shahripour,D. Holland, J.R. Rubin, C. Humblet, J. Fergus, J. Marks, S. Hubbell, R.Herrera, A.R. Saltiel, and T.K. Sawyer

New RGDAmphiphilic Cyclic Peptide and New RGD-Mimetic ConstrainedDiketopiperazines

Jean-François Pons, Mamadou Sow, Frédéric Lamaty, Jean-LucFauchère, Annie Molla, Philippe Viallefont, and René Lazaro

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A Pharmacophore Model of a Novel Hematoregulatory Peptide, SK&F107647 and Design of Peptidomimetic Analogs

P.K. Bhatnagar, E.K. Agner, D. Alberts, J. Briand, L.J.F. Callahan,A.S. Cuthbertson, H. Fjerdingstad, D. Heerding, J. Hiebl, W.F.Huffman,M. Husbyn, A.G. King, S. LoCastro, D. Løvhaug, L.M. Pelus,G. Seibel, and J. S. Takata

Design and Synthesis of Potent and Selective Peptidomimetic VitronectinReceptor Antagonists

Jochen Knolle, Roland Baron, Gerhard Breipohl, Pierre Broto, TomGadek, Jean F. Gourvest, Glenn R. Hammonds, Anusch Peyman,Karl H. Scheunemann, Hans U. Stilz, and Volkmar Wehner

Structure-Based Design of Small Molecule Protein-Tyrosine PhosphataseInhibitors

Zhu-Jun Yao, Bin Ye, He Zhao, Xinjian Yan, Li Wu, David Barford,Shaomeng Wang, Zhong-Yin Zhang, and Terrenes R. Burke, Jr.

Structure-Activity Relationships and Spectroscopic Insights into a Series ofRetro-Inverso Tachykinin NK-1 Receptor Antagonists

A. Sisto, R. Cirillo, B. Conte, C.I. Fincham, E. Monteagudo, E. Potier,R. Terracciano, F. Cavalieri, M. Venanzi, and B. Pispisa

Immunologically Active Mimetics of Muramyl DipeptideDanijel Kikelj, Alenka Rutar, Irena Merslavi , Lu ka Povši , and AntonŠtalc

Peptidomimetic Tyrosine Kinase Inhibitors Induce Non Apoptotic, Clarke-IIIType Programmed Cell Death

György Kéri, László Ôrfi, Gergely Szántó, Judit Érchegyi, FerencHollósy, Miklós Idei, Anikó Horváth, István Teplán, Aviv Gazit,Zsolt Szegedi, Béla Szende

SAR of a series of Related Peptidomimetics Derived from a NovelHematoregulatory Peptide, SK&F 107647

J.F. Callahan, D. Alberts, J.L. Burgess, L. Chen, W.F.Huffman,A.G. King, S. LoCastro, L.M. Pelus, and P.K. Bhatnagar

Applications of Tropane-Based PeptidomimeticsPhilip E. Thompson, David L. Steer, Kerry A. Higgins, Marie-IsabelAguilar, and Milton T.W. Hearn

Structure-Activity Relationship Studies of Dialkylamine DerivativesExhibiting Wide Spectrum Antimicrobial Activities

U.P. Kari, S.R. Maddukuri, M.T. MacDonald, L.M. Jones,D.L. MacDonald, and W.L. Maloy

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Identification of Prototype Peptidomimetic Agonists at the Human MelanocortinReceptors, MC1R and MC4R

Carrie Haskell-Luevano, Tomi K. Sawyer, Mac E. Hadley, Victor J.Hruby, and Ira Gantz

Cyclic Somatostatins Containing Benzyl-o-AMPA as a Cis Peptide BondMimic

Dirk Tourwé, Valerie Brecx, Jo Van Betsbrugge, and PatriciaVerheyden

Alpha-Helix Nucleation Between Peptides Using a Covalent Hydrogen BondMimic

Elena Z. Dovalsantos, Edelmira Cabezas, and Arnold C. Satterthwait

Development of Inhibitors of MAdCAM- InteractionsH.N. Shroff, C.F. Schwender, A.D. Baxter, N. Hone, N.A. Cochran,D.L. Gallant, and M.J. Briskin

Synthesis of Cyclic RGD-Tetra-Peptoids and Optimization of theSubmonomer Solid Phase Coupling Protocol

Jorg S. Schmitt, S.L. Goodman, A. Jonczyk, and Horst Kessler

Reduced Amide Bond Pseudopeptides Induce Antibodies Against NativeProteins of Plasmodium falciparum

José Manuel Lozano, Fabiola Espejo, Diana Diaz, Fanny Guzmán,Julio C. Calvo, Luz M. Salazar, and Manuel Elkin Patarroyo

Inhibition of Ras Farnesyl Transferase by Histidine-(N-Benzylglycinamide)Type Molecules

Kevon R. Shuler, Daniele M. Leonard, Dennis J. McNamara, Jeffrey D.Scholten, Judith S. Sebolt-Leopold, and Annette M. Doherty

Synthesis of Dipeptide Secondary Structure MimeticsMasakatsu Equchi, Hwa-Ok Kim, Benjamin S. Gardner, P. DouglasBoatman, Min S. Lee, Hiroshi Nakanishi, and Michael Kahn

Design and Synthesis of Nanomolar -Opioid Selective Non-Peptide MimeticAgonists Based on Peptide Leads

Subo Liao, Mark D. Shenderovich, Josue Alfaro-Lopez, DagmarStropova, Keiko Hosohata, Peg Davis, Kevin A. Jernigan, Frank Porreca,Henry I. Yamamura, and Victor J. Hruby

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Development of the New Potent Non-Peptide GpIIb/IIIa Antagonist NSL-95301 by Utilizing Combinatorial Idea

Yoshio Hayashi, Takeo Harada, Jun Katada, Akira Tachiki, KiyokoIijima, Tohru Asari, Isao Uno, and Iwao Ojima

A flexible Strategy for the Incorporation of Ureas into Peptide LinkagesJ.A. Kowalski, and M.A. Lipton

Session IV. Synthetic MethodsOn-resin N-methylation circumvents a Deletion Peptide Formed during theSynthesis of Cyclosporin Analogs

Prakash Raman, Yvonne M. Angell, George R. Flentke, and Daniel H.Rich

Synthetic Approaches to Elucidate Roles of Disulfide Bridges in Peptidesand Proteins

George Barany

Synthesis of Cyclopsychotride by Orthogonal Ligation Using UnprotectedPeptide Precursor

Yi-An Lu and James P. Tam

Methionine as the Ligation Site in the Orthogonal Ligation of UnprotectedPeptides

Qitao Yu and James P. Tam

Low Scale Multiple Array Synthesis and DNA Hybridization of PeptideNucleic Acids

Ralf Hoffmann, Hildegund C.J. Ertl, Anne Marie Pease, Zhenning He,Giovanni Rovera, and Laszlo Otvos, Jr.

Intramolecular Orthogonal Ligation for the Synthesis of Cyclic PeptidesChuan-Fa Liu, Chang Rao, and James P. Tam

A New Approach to Phosphonopeptide AnalogsMaria de Fatima Fernandez, Joseph C. Kappel, and Robert P. Hammer

Protected amino acid chlorides: Coupling reagents suitable for the mosthighly hindered systems

Michael Beyermann, Dumitru Ionescu, Petra Henklein, Ayman El-Faham,Holger Wenschuh, Michael Bienert, and Louis A. Carpino

Stereoselective synthesis of highly topographically constrainedisopropyl substituted aromatic amino acids

Yinglin Han, Jun Lin, Subo Liao, Wei Qiu, Chaozhong Cai, andVictor J. Hruby

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Development of a New Class of Protecting Groups for Use in Solid PhasePeptide Synthesis.

Amelie H. Karlström and Anders E. Undén

Sequential Orthogonal Ligation for the Synthesis of DefensinChristophe Hennard and James P. Tam

A Facile Metal Ion-Assisted Amidation on Solid SupportsKalle Kaljuste and James P. Tam

Sequence Assisted Peptide Synthesis (SAPS): a Structural Evaluation of theTechnology

B. Due Larsen, A. Holm, D.H. Christensen, and O. Faurskov Nielsen

The Design of Congener Breaking Sets to Determine the Function of AminoAcid Residues in Biologically Active Peptides

James A. Burton, Timothy B. Frigo, and Bore G. Raju

Application of Different Coupling and Deprotection Conditions in theSynthesis of “Difficult Sequences”

M. Villain, P.L. Jackson, N.R. Krishna, and J.E. Blalock

An Artificial Receptor for a Tri(Histidine) LigandSanku Mallik, Suguang Sun, Jennifer Saltmarsh, and Ipsita Mallik

Comparative Studies of Racemization during Peptide SynthesisTodd T. Romoff, Thuy-Anh Tran, and Murray Goodman

A Novel Approach for SPPS of Compounds with an Amidino-Group in theC-Terminal Residue Using Trityl Resins

Torsten Steinmetzer, Andrea Schweinitz, Lydia Seyfarth, SiegmundReißmann, and Jörg Stürzebecher

Mild Methods for the Synthesis of Peptide Aldehydes Directly from ThioesterResin

Aleksandra Wyslouch-Cieszynska and James P. Tam

Synthesis of Cyclic Ureas and Cyclic Thioureas from Acyl DipeptidesAdel Nefzi, Marc A. Giulianotti, Edward Brehm, Christa C. Schoner,Vince T. Hamashin, and Richard A. Houghten

Tri-t-Butyl-DTPA: a Versatile Synthon for the Preparation of DTPA-Containing Peptides by Solid Phase

Ananth Srinivasan and Michelle A. Schmidt

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Intramolecular Migration of the Protecting Group ofDiaminopropionyl to the During Fmoc Solid Phase Synthesis

Ananth Srinivasan, R. Randy Wilhelm, and Michelle A. Schmidt

Intentional Syntheses of Disulfide-Mispaired Isomers of Conotoxin SI andSIA

Balazs Hargittai and George Barany

S-Xanthenyl Side-Chain Anchoring for Solid-Phase Synthesis of Cysteine-Containing Peptides

Balazs Hargittai, Yongxin Han, Steven A. Kates, and George Barany

Isolation, Characterization, and Synthesis of a Trisulfide Related to theSomatostatin Analog Lanreotide

Lin Chen, Steven R. Skinner, Thomas D. Gordon, John E. Taylor, GeorgeBarany, and Barry A. Morgan

Novel Safety-Catch Protecting Groups and Handles Cleavable byIntramolecular Cyclization

Chongxi Yu and George Barany

Synthesis of Conformationally Constrained Peptides Using the HeckReaction

David E. Wright

A Facile Synthesis of 3-Substituted Pipecolic AcidsGergely M. Makara and Garland R. Marshall

Rapid Thioester Couplings Mediated by New Uronium SaltsHartmut Echner and Wolfgang Voelter

Chemical Synthesis, Purification and Characterization of a 107 ResidueFragment of the Prion Protein

Haydn L. Ball, Michael A. Baldwin, Tatiana Bekker, Paolo Mascagni,David King, and Stanley B. Prusiner

Problems Encountered with the Synthesis of a Glycosylated HydroxylysineDerivative Suitable for Fmoc-Solid Phase Peptide Synthesis

Henriette A. Remmer and Gregg B. Fields

Efficient Assembly of Stable Site-Directed Fluorescence Labeled PeptidesHolger Wenschuh, Ulrich Schaible, Stephanie Lamer, Michael Bienert,and Eberhard Krause

Solid Phase Synthesis of Lanthionine PeptidesJ.P. Mayer, J. Zhang, S. Gröger, and C.F. Liu

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Synthesis of (-methyl Aspartic AcidsGuoxia Han, Andrew Burritt, Jung-Mo Ahn, and Victor J. Hruby

Total Solid-Phase Synthesis of Human Cholecystokinin (CCK)-39K. Kitagawa, C. Aida, H. Fujiwara, T. Yagami, and S. Futaki

Studies on Synthesis of Peptides with C-Terminal Glutamine Para-nitroanilide

Lili Guo, Dongxia Wang, Patrick J. Edwards, Navayath Shobana, andRoger W. Roeske

Solid Phase Synthesis of Peptide Nucleic Acid-Peptide ConjugatesLynn Mayfield, Revathi Katipally, Carla Simmons, and David R.Corey

Solid Phase Protein Synthesis by Chemical Ligation of Unprotected PeptideSegments in Aqueous Solution

Lynne E. Canne, Darren A. Thompson, Reyna J. Simon, and Stephen B. H.Kent

Amino Acids with Alkyloxyaryl-Keto Function in their Side ChainsMaria A. Bednarek

Solid-Phase Synthesis via 5-Oxazolidinones. Ring Opening Reactions withAmines and Reaction Monitoring by Single Bead FT-IR Microspectroscopy

Roger E. Marti, Mary Sue Martin, Bing Yan, and Mark A. Jarosinski

Synthesis and Applications of a Bis-Sulfonyl Handle for Solid-PhaseSynthesis of Peptides

Marta Planas, Susumu Funakoshi, Eduard Bardají, and FernandoAlbericio

Side Reactions During Synthesis of p-Benzoylphenylalanine ScannedAnalogs of the Yeast Tridecapeptide Pheromone

Michael Breslav, Boris Arshava, Jeffrey M. Becker, and Fred Naider

Diaminopimelate-Containing Isopeptides are Cleavable by LeucineAminopeptidase and Metalloproteinases in Tumors

Yoshimitsu Yamazaki, Michael Savva, and Michael Mokotoff

Synthesis and Optical Properties of Cyclic Bis-Cysteinyl-Peptides and theirLinear Precursors with a Built-in Light-Switch

Michaela Schenk, Sabine Rudolph-Böhner, Josef Wachtveitl, ThomasNägele, Dieter Oesterhelt, and Luis Moroder

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Cyclodextrin as Carrier of Bioactive PeptidesNorbert Schaschke, Stella Fiori, Daniel Fourmy, and Luis Moroder

Facile Steroselective Synthesis of Acids from the CorrespondingAmino Acids

Pavel Majer, Martin Smrcina, Eva Majerová, Tatiana A. Guerassina, andMichael A. Eissenstat

Unnatural Peptide Synthesis (UPS): a Positional Scan StudyPeteris Romanovskis, David Mendel, Martin J. O’Donnell, William C.Scott, Arno F. Spatola, and Changyou Zhou

Preparation of Peptide Thioester Segments Using Fmoc-Solid-Phase PeptideSynthesis and Application of the Thioester Ligation Strategy to theConstruction of TASP Molecules

Shiroh Futaki, Koji Sogawa, Masayuki Fukuda, Mineo Niwa, andHironobu Hojo

Racemization Induced by Excess Base During Activation with Uronium SaltsJo-Ann Jablonski, Russel Shpritzer, and Stephen P. Powers

Synthesis and Characterization of a Novel Tryptophan DerivativeTed J. Gauthier, Bo Liu, Guillermo Morales, and Mark L. McLaughlin

On Resin Preparation of C-Terminal Peptide Amides, Analogs of theNematode Neuropeptide PF1, , by Application of a

Cysteine-Specific Precursor CleavageTeresa M. Kubiak, Alan R. Freidman, and Martha J. Larsen

Synthesis of a Series of “Cationic”, Orthogonally Protected,Disubstituted Amino Acids

T.S. Yokum, M.G. Bursavich, S.A. Piha-Paul, D.A. Hall, and M.L.McLaughlin

Synthesis of Nα -t-Boc-Benz[f]Tryptophan: An Intrinsic/ExtrinsicFluorescent Probe

T.S. Yokum, P.K. Tungaturthi, and M.L. McLaughlin

Synthesis of HIV-1 Protease Analog by Ligation of Bromoacetyl andMercaptoethylamide Peptide Prepared Using Disulfide Linkage to Solid-Support

Yoshiaki Kiso, Tooru Kimura, Yoichi Fujiwara, Naoki Nishizawa, HikaruMatsumoto, Masamichi Kishida, Kenichi Akaji, and Haruo Takaku

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An Efficient Preparation of the Potent and Selective Pseudopeptide ThrombinInhibitor, Inogatran

Wayne L. Cody, John X. He, Patrice Préville, Micheline Tarazi, M.Arshad Siddiqui, and Annette M. Doherty

Application of Novel Organophosphorus Compounds as Coupling Reagentsfor the Synthesis of Bioactive Peptides

Yun-hua Ye, Chong-xu Fan, De-yi Zhang, Hai-bo Xie, Xiao-lin Hao, andGui-lin Tian

Minimization of Cysteine Racemization During Stepwise Solid-PhasePeptide Synthesis

Yvonne M. Angell, Yongxin Han, Fernando Albericio, and George Barany

Solid Phase Synthesis of N-Methyl Amino Acids: Application of theFukuyama Amine Synthesis

Lihu Yang and Kuenley Chiu

Novel Solid-Phase Reagents for Facile Formation of IntramolecularDisulfide Bonds in Peptides Under Mild Conditions

Ioana Annis and George Barany

Fmoc-2-Aminopalmitic Acid for the Synthesis of Lipopeptides with anHydrophobic Chain on a C-C Bond

Anna M. Papini, Silvia Mazzucco, Elena Nardi, Mario Chelli, MauroGinanneschi, and Gianfranco Rapi

Session V. Structure, Folding and Conformational AnalysisFolding of a Predominantly β-sheet Protein with a Central Cavity

P.L. Clark, M. Sukumar, Z.P. Liu, J. Rizo, B.F. Weston, K.S. Rotondi,and L.M. Gierasch

Insights into the Molecular Mechanisms of Protein Folding and MisfoldingSheena E. Radford

Prediction of Protein Transmembrane Segments Using a HydrophobicityScale Derived from Hydrophobic Peptides

Li-Ping Liu, Chen Wang, and Charles M. Deber

Structure, Function and Modeling of Human Endothelin and Its PrecursorPolypeptide, BigET: Targets for Rational Drug Design

Bonnie A. Wallace and R.W. Janes

3D Modeling for TM Receptors: Problems and PerspectivesGregory V. Nikiforovich, Stan Galaktionov, Vladimir M. Tseitin, David R.Lowis, Mark D. Shenderovich, and Garland R. Marshall

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Multicyclic Side-Chain Bridged Peptides Designed for StabilizationJohn W. Taylor, Guihua Guo, and Chongxi Yu

Natural Selection with Self Replicating PeptidesS.Q. Yao, I. Ghosh, and J.A. Chmielewski

Exploring the Foldability and Function of Insulin by Combinatorial PeptideChemistry

Ming Zhao, Satoe Nakagawa, Qingxin Hua, and Michael A. Weiss

Characterization of Transforming Growth Factor Alpha Binding to EpidermalGrowth Factor Receptor Through NMR Structure Determination and NOEAnalysis Methods

Campbell McInnes, David W. Hoyt, Maureen O’Connor-McCourt, andBrian D. Sykes

Vibrational and Electronic Circular Dichroism Study of 310-HelicalStabilization in Blocked Peptides

Gorm Yoder, T.A. Keiderling, Alessadra Polese, Fernando Formaggio,Marco Crisma, Claudio Toniolo, Q.B. Broxterman, and Johan Kamphuis

First Peptide-Based System of Rigid Donor, Rigid Acceptor, and RigidInterchromophore Spacer: a Conformational and Photophysical Study

Claudio Toniolo, Fernando Formaggio, Marco Crisma, Jean-PaulMazaleyrat, Michel Wakselman, Clifford George, Judith L. Flippen-Anderson, Basilio Pispisa, Mariano Venanzi, and Antonio Palleschi

Correlation of Kinetic Data with Crystallographic Structures of AsparticProteinases

Ben M. Dunn, Kohei Oda, Marina Bukhtiyarova, Deepa Bhatt, ChetanaRao-Naik, W. Todd Lowther, Paula E. Scarborough, Brian M. Beyer,Jennifer Westling John Kay, Nora Cronin, and Tom Blundell

Structural Characterization of Two-Stranded Anti-Parallel Peptides forDNA Major Groove Recognition

Bing Y. Wu and Laurence H. Hurley

Conformation and Activity of Antimicrobial Peptides Related to PGLaJack Blazyk, Janet Hammer, Amy E. Kearns, U. Prasad Kari, and W. LeeMaloy

Structure-Activity Studies on a Circular Protein DomainJulio A. Camarero, Joanna Pavel, and Tom W. Muir

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Folding and Aggregation in Mixed Dimers of Gramicidin DWilliam L. Duax, Brian M. Burkhart, David A. Langs, and Walter A.Pangborn

RS-66271, a Clinical Candidate Derived from Parathyroid Hormone RelatedProtein: the Role of Enhanced Amphiphilic Helicity

Maria Pellegrini, Alessandro Bisello, Michael Rosenblatt, MichaelChorev, and Dale F. Mierke

Identification of a Minimal Peptide Sequence of Islet Amyloid Polypeptide(IAPP) with Amyloidogenic and Cytotoxic Properties

Aphrodite Kapurniotu, Jürgen Bernhagen, Wolfgang Fischle, SaulTeichberg, Wolfgang Voelter, and Richard Bucala

Substrate Specificity and Mechanism of Activation of Hepatitis C VirusProtease

Elisabetta Bianchi, Andrea Urbani, Raffaele De Francesco, ChristianSteinkühler, and Antonello Pessi

The Allosteric-type Mechanism of Tetanus Toxin Metalloprotease ActivityDetermines Its Substrate Specificity

Fabrice Cornille, Loïc Martin, Christine Lenoir, Didier Cussac, BernardP. Roques, and Marie-Claude Fournié-Zaluski

Structure Activity Studies of Macrophage Migration Inhibitory Factor Showa Functional Role for Cysteine Residues

Jürgen Bernhagen, Robert Kleemann, Aphrodite Kapurniotu, RichardBucala, and Herwig Brunner

Secondary and Tertiary Fold of the Human Parathyroid Hormone 1-34 inDifferent Environments as a Pathway to Bioactive Conformation

Maria Pellegrini, Stefano Maretto, Miriam Royo, Michael Rosenblatt,Michael Chorev, and Dale F. Mierke

Three-Dimensional Models of Opioid Pharmacophore: Molecular Modelingand QSAR Study of Peptide and Non-Peptide Ligands

Mark D. Shenderovich, Subo Liao, Xinhua Qian, and Victor J. Hruby

A Chromophoric Study of Zinc Coordination and Conformer Selectivity ofthe Human Insulin Hexamer in Solution

Mark L. Brader

Amide NH Shift Gradients: Quantitating Peptide Strucure/DisorderTransitions

Jonathan W. Neidigh, Scott M. Harris, Hui Tong, Gregory M. Lee,Zhihong Liu, and Niels H. Andersen

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xxii

Predicting the Conductance Properties for Ion Channel Structural Models Usingthe HOLE Program

Oliver S. Smart

Molecular Dynamics Simulation of Epidermal Growth Factors in AqueousSolution

Charles R. Watts, Sándor Lovas, and Richard F. Murphy

Engineering of Snake Venom Cardiotoxin by Computer Modeling andChemical Synthesis Approach

Shui-Tein Chen, Chi-Yue Wu, and Kung-Tsung Wang

In Search of the Earliest Events of hCG Folding: Structural Studies of the 60-87 Peptide Fragment

S. Sherman, L. Kirnarsky, O. Prakash, H.M. Rogers, R.A.G.D. Silva, T.A.Keiderling, D.D. Smith, A.M. Hanly, F. Perini, and R.W. Ruddon

Synthetic Peptides from Putative Amphipathic Strand Sequences ofApolipoprotein B-100 Associate with Lipid in the Strand Conformation

Vinod K. Mishra, Manjula Chaddha, G.M. Anantharamaiah, MayakondaN. Palgunachari, Krishnan K. Chittur, Sissel Lund-Katz, Michael C.Phillips, and Jere P. Segrest

Proline Puckering and a cis-trans Isomerization of Proline-ContainingPeptides

Young Kee Kang, Seong Jun Han, and Jong Suk Jhon

Retention of Cis-Proline Rotamer in a Small Fragment of RNaseA Containing a Non-Natural Proline Analog - an NMR Study

Yue-Jin Li, Cathy C. Lester, David M. Rothwarf, Jin-Lin Peng, TheodoreW. Thannhauser, Lianshan Zhang, James Tam, and Harold A. Scheraga

Phosphorylation Alters the Three Dimensional Structure of the CarboxylTerminal of Bovine Rhodopsin

Arlene D. Albert, Phillip L. Yeagle, James L. Alderfer, Marc Dorey, ToddVogt, Nilaya Bhawsar, Paul A. Hargrave, J. Hugh McDowell, and AnatolArendt

Conformational Calculations Restrained by NMR and Fluorescence Data onFunctionalized Aib-Based Peptides

Basilio Pispisa, Maria E. Amato, Antonio Palleschi, Mariano Venanzi,Giancarlo Zanotti, and Anna L. Segre

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Long-Distance REDOR NMR Measurements for Determination of SecondaryStructure and Conformational Heterogeneity in Peptides

Boris Arshava, Michael Breslav, Octavian Antohi, Ruth E. Stark, Joel R.Garbow, Jeffrey M. Becker, and Fred Naider

Interpretation of the Fluorescence Decay Characteristics of CyclicCasomorphin Analogs Based on Theoretically Calculated Ensembles of theirLow Energy Conformers

B.C. Wilkes, B. Zelent, H. Malak, R. Schmidt, and P.W. Schiller

Synthesis of the Putative Sixth Transmembrane Helix of the Neurokinin-1Receptor and its Structural Analysis in Phospholipid Bilayer Vesicles

Chinchi C. Chen, and Garland R. Marshall

Distinguishing in a Lipopeptaibol Antibiotic Using the Amino

Acid TOAC and ESR.Vania Monaco, Claudio Toniolo, Fernando Formaggio, Marco Crisma,Paul Hanson, Glenn L. Millhauser, Clifford George, Judith L. Flippen-Anderson, Sylvie Rebuffat, and Bernard Bodo

3D Structure of the Anti-AChR Fv Antibody Fragment Complexed to theAntigen: A Homology and Molecular Modelling Approach

Piotr Orlewski, Jens Kleinjung, Avgi Mamalaki, Christos Liolitsas,Socrates J. Tzartos, Vassilios Tsikaris, Maria Sakarellos-Daitsiotis,Constantinos Sakarellos, and Manh-Thong Cung

Parathyroid Hormone-Related Protein Derived Mono- and Bi-CyclicAgonists and Antagonists: A Conformational Comparison

Stefano Maretto, Elisabetta Schievano, Evaristo Peggion, StefanoMammi, Alessandro Bisello, Michael Chorev, Michael Rosenblatt, andDale F. Mierke

The NMR Structure of a Cyclic V3 Loop Peptide that Binds Tightly to aMonoclonal Antibody that Potently Neutralizes HIV-l

Edelmira Cabezas, and Arnold C. Satterthwait

Folding of the Second Extracellular Loop of the Myelin Proteolipid Protein(PLP)

Ingrid Dreveny and Elisabeth Trifilieff

An Improved Template for the Initiation of Peptide HelicesEvan T. Powers, Peter Renold, Sherri Oslick, and D.S. Kemp

xxiii

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xxiv

Conformational Studies of a PTH/PTHrP HybridsStefano Mammi, Lara Pauletto, Evaristo Peggion, Vered Behar,Michael Rosenblatt, and Michael Chorev

Synthesis and Conformational Anlysis of C- and N-GlycopeptidesFred Burkhart, Gerhard Hessler, and Horst Kessler

Lactam Cyclization [i to (i+4)] for Nucleation/Stabilization ofGal Bitan, Maria Pellegrini, Michael Chorev, and Dale F. Mierke

Molecular Modeling and Design of Metal Binding Template AssembledSynthetic Proteins (TASP)

Gregory V. Nikiforovich, Christian Lehmann, and Manfred Mutter

Syntheses, Conformational Analysis and the Bioactivities of the LanthionineAnalogs of a Cell Adhesion Modulator

Haitao Li, Xiaohui Jiang, and Murray Goodman

Utilization of a Reporting Conformational Template in Probing the Phe-HisInteraction in the Short Alanine-Rich Peptide Helices

Kwok Yin Tsang and Daniel S. Kemp

Structure-Activity Studies on the AbI-SH2 DomainMaria C. Pietanza and Tom W. Muir

Design and Use of Amphiphilic Peptides in Liposomes as pH-TriggeredReleasing Agents

M.L. Brickner, C. Yusuf, K.M. Vogel, and J.A. Chmielewski

NMR Structure Determination and DNA Binding Properties of GCN4Peptidomimetics Designed for Initiation and Stabilization

Min Zhang, Bingyuan Wu, Jean Baum, and John Taylor

Synthesis and Conformational Analysis of Axinastatin 5 and DerivativesOliver Mechnich, Gerhard Hessler, Michael Bernd, Bernhard Kutscher,and Horst Kessler

On the Energetics of the Heterodimerization of the Max and c-Myc LeucineZippers

P. Lavigne, L.H. Kondejewski, M.E. Houston Jr., R.S. Hodges, and C.M.Kay

Synthesis and Conformational Analysis of Cyclic-Hexapeptides Related toSomatostatin Incorporating Novel Peptoid Structures

Thuy-Anh Tran, Ralph-Heiko Mattern, and Murray Goodman

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The Importance of Residue B8 in Insulin Activity, Structure and FoldingSatoe H. Nakagawa, Ming Zhao, Qin Xin Hua, and Michael A. Weiss

Opioidmimetic Peptides Containing α -Aminoisobutyric AcidSharon D. Bryant, Remo Guerrini, Severo Salvadori, Clementina Bianchi,Roberto Tomatis, Martti Attila, and Lawrence H. Lazarus

Circular Dichroism Study of the Interaction of Synthetic J Protein ofBacteriophage with Single-Stranded DNA

Shin Ono, Takayuki Okada, Saburo Aimoto, Ken-Ichi Kodaira, TakayoshiFujii, Choichiro Shimasaki, and Toshiaki Yoshimura

V3 Loop of HIV gp120 Protein: Molecular Modeling of 3D StructuresInteracting with Cell Proteins

Stan Galaktionov, Gregory V. Nikiforovich, and Garland R. Marshall

Conformational Studies of a -substituted PTHrP -derived AntagonistContaining Lactam-Bridged Side-Chains

Stefano Maretto, Elisabetta Schievano, Stefano Mammi, AlessandroBisello, Chizu Nakamoto, Michael Rosenblatt, Michael Chorev, andEvaristo Peggion

Cold Denaturation Studies of (LKELPKEL)n Peptide Using Vibrational andElectronic Circular Dichroism Spectroscopic Techniques

R.A.G.D. Silva, Vladimir Baumruk, Petr Pancoska, T.A. Keiderling,Eric Lacassie, and Yves Trudelle

Solution Structure of Human Salivary StatherinTarikere L. Gururaja, Gowda A. Naganagowda, and Michael J. Levine

Interaction of Melittin with Phospholipid Monolayer Modified Silica SupportTzong-Hsien Lee, Hans-Jürgen Wirth, Patrick Perlmutter, and Marie-Isabel Aguilar

Prediction of Intramembrane Regions in Transmembrane HelicesVladimir M. Tseitin and Gregory V. Nikiforovich

Synthesis of Gramicidin Analogs with Conformational ConstrainedDipeptides

Wei-Jun Zhang, Jeff Kao, Eduardo Groissman, and Garland R. Marshall

Conformational Studies of Rat Brain Sodium Ion Channel Segment IS4 inDifferentMedia

Zhenwei Miao, Yun Jiang, Saburo Aimoto, Xiaojie Xu, and Youqi Tang

xxv

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xxvi

Identification of a Novel Human CD8 Surface Region Involved in MHCClass I Binding

Song Li, Swati Choksi, Simei Shan, Jimin Gao, Robert Korngold, andZiwei Huang

Surveying the Protein Folding Landscape: Equilibrium Models for PartiallyFolded Intermediates of Bovine Pancreatic Trypsin Inhibitor (BPTI)

Christopher M. Gross, Clare Woodward, and George Barany

Structure Acivity Studies of Normal and Retro Pig Cecropin- MelittinHybrids

Padmaja Juvvadi, Satyanarayana Vunnam, Barney Yoo, and R.B.Merrifield

Session VI. Receptor-Ligand interactionsA Peptide Mimetic of Erythropoietin: Critical Residues and Description of aMinimal Functional Epitope

Dana L. Johnson, Francis X. Farrell, Frank J. McMahon, Jennifer Tullai,Francis P. Barbone, Steven A. Middle ton, Kenay Hoey, Oded Livnah,Nicholas C. Wrighton, William J. Dower, Linda S. Mulcahy, Enrico A.Stura, Ian A. Wilson, and Linda K. Jolliffe

Structure of Rhodopsin-Bound C-Terminal of TransducinOleg G. Kisselev, Yang C. Fann, N. Gautam, and Garland R. Marshall

Molecular Dissection of the Receptor: the N-Terminal Domain ofthe γ2 Subunit is Essential for Benzodiazepine Binding and Subunit Assembly

Andrew J. Boileau, Amy Kucken, Amy R. Evers, and Cynthia Czajkowski

Glucagon Receptor Structure and Function: Probing the Putative HormoneBinding Site with Receptor Chimeras

Cecilia G. Unson, Aaron M. Cypess, Cui-Rong Wu, Connie P. Cheung,and R.B. Merrifield

A New Class of Dipeptide Derivatives that are Potent and Selective OpioidAgonists

P.W. Schiller, G. Weltrowska, I. Berezowska, C. Lemieux, N.N. Chung,K.A. Carpenter, and B.C. Wilkes

Discovery of Small Non-Peptidic CD4 Inhibitors as NovelImmunotherapeutics

Song Li, Jimin Gao, Takashi Satoh, Thea M. Friedman, Andrea E. Edling,Ute Koch, Swati Choksi, Xiaobing Han, Robert Korngold, and ZiweiHuang

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Biochemistry and Biology of PhospolipaseGraham Carpenter, Qun-sheng Ji, and Debra Horstman

Tumor Cell Interactions with Type IV Collagen: Synthetic PeptideDissection of Post-Adhesion Signal Transduction Mechanisms

Janelle L. Lauer, and Gregg B. Fields

Somatostatin Receptor Antagonists Based on a Mixed Neuromedin BAntagonist/Somatostatin Agonist

David H. Coy, Rahul Jain, William A. Murphy, Wojciech J. Rossowski,Joseph Fuselier, and John E. Taylor

The Origin of Specificity in the Opioid Receptor FamilyIrina D. Pogozheva, Andrei L. Lomize, and Henry L. Mosberg

Mapping of the Interleukin-l0/Interleukin-10 Receptor Combining Site UsingStructually Different Peptide Scans

Ulrich Reineke, Robert Sabat, Hans-Dieter Volk, and Jens Schneider-Mergener

Design and Synthesis of Specific Proline-Rich Peptides with High Affinityfor Grb2

Didier Cussac, Fabrice Cornille, Gilles Tiraboschi, Christine Lenoir,Bernard Roques, and Christiane Garbay

N-Terminal Myristoylation of HBV Pre-Sl Domain Affects Folding andReceptor Recognition

Menotti Ruvo, Sandro De Falco, Antonio Verdoliva, Angela Scarallo, andGiorgio Fassina

High Affinity Peptides as Antagonists ofHuman IgE Binding

Waleed Danho, Raymond Makofske, Joseph Swistok, Michael Mallamaci,Mignon Nettleton, Vincent Madison, David Greeley, David Fry, and JaremaKochan

Highly Potent Human Parathyroid Hormone AnalogsJesse Z. Dong, Chizu Nakamoto, Michael Chorev, Barry A. Morgan,Michael Rosenblatt, and Jacques-Pierre Moreau

Monitoring Binding Interactions of Peptide-Peptide, Peptide-Protein, Ligand-Protein and Substrate-Enzyme by NILIA-CD Spectroscopy

Giuliano Siligardi, and Rohanah Hussain

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Peptide Libraries with Free Carboxy-Terminus Used to Characterize EpitopesRecognized by PDZ-Domains

Ulrich Hoffmüller, Rudolf Volkmer-Engert, Mark Kelly, HartmutOschkinat, and Jens Schneider-Mergener

Functional Site Studies with Peptide Segments of Cdk Inhibitory ProteinsPeter P. Roller, Feng-Di T. Lung, Masato Mutoh, and Patrick M.O’Connor

Expression of C5a Receptors (CD 88) on Human Bronchial Epithelial Cells(HBEC): C5a-Mediated Release of IL-8 upon HBEC Exposure to CigaretteSmoke

Anthony A. Floreani, Art J. Heires, Laurel Clark-Pierce, Lisbeth Welniak,Amanda Miller-Lindholm, Stephen I. Rennard, Edward L. Morgan, andSam D. Sanderson

Mapping and Characterization of Epitopes Recognized by WW DomainsUsing Cellulose-Bound Peptide Libraries

Ulrich Hoffmüller, Hartmut Oschkinat, and Jens Schneider-Mergener

Biological and Physicochemical Properties of UrocortinAndreas Rühmann, Ines Bonk, Andreas K.E. Köpke, and Joachim Spiess

Towards a Rational Approach in the Finding of Potent Peptide Ligands forGrb2 SH2

C. García-Echeverría, B. Gay, P. Furet, J. Rahuel, H. Fretz, J.Schoepfer, and G. Caravatti

Multivalent Carbohydrate-Linked Peptides Interfere with Adherence ofCandida albicans to Asialo-GMl Receptor: Toward the Design of Anti-AdhesinTherapeutics

C.M. Charles Yang, Wah Y. Wong, Ole Hindsgaul, Randall T. Irvin, andRobert S. Hodges

Development of Somatostatin Agonists with High Affinity and Specificity forthe Human and Rat Type 5 Receptor Subtype

David H. Coy and John E. Taylor

Properties of GnRH Conjugates In VivoImre Mezö, B. Vincze, G. Tóth, J. Pató, D. Gaál, T. Kremmer, A.Kálnay, E. Gulyás, I. Teplán, F. Ötvös, S. Lovas, R.F. Murphy, and I. Pályi

Phospholipid Vesicle Binding by an Amphiphilic Structure fromSerum Apolipoprotein B-100

Jinliang Lu and John W. Taylor

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Stability and Binding of SH3 Domain of Bruton’s Tyrosine KinaseJya-Wei Cheng, Himatkumar V. Patel, Shiou-Ru Tzeng, and Chen-Yee Liao

The Interaction Between Monoclonal Antibody 4A5 and Fibrinogen GammaChain Peptides Studied by Nuclear Magnetic Resonance

Michael Blumenstein and Gary R. Matsueda

A Potent Synthetic Dimeric Peptide Agonist of the Erythropoietin ReceptorPalaniappan Balasubramanian, Qun Yin, Surekha Podduturi, Nicholas C.Wrighton, and William J. Dower

Binding Studies of Cytokines rhGM-CSF and rhIL-3 with a PeptideFragment of hGM-CSF Receptor by Non-Immobilised LigandInteraction Assay (NILIA) Using Circular Dichroism(CD)

Rohanah Hussain, Paolo Rovero, Claudia Galoppini, and GiulianoSiligardi

Synthesis, Bioactivity, 2D NMR and ESR of Angiotensin II and Its SpinLabelled Derivative

Xiaoyu Hu, Rui Wang, Xiaoxu Li, and Jianheng Shen

Structure-Function Studies on Synthetic Tetrapeptide Analogs of AVP(4-8)Ke-Yin Ma and Yu-Cang Du

Development of Feeding and Y-1 NPY Receptor AntagonistsZ. Tao, F. Peng, S. Sheriff, P. Eden, J. Taylor, W.T. Chance, andA. Balasubramaniam

Receptor 3D Homology Molecular Modeling and In Vitro MutagenesisIdentify Putative Melanocortin (hMC1R) Agonist Ligand-ReceptorInteractions and a Proposed Mechanism for Receptor Activation

Carrie Haskell-Luevano, Ying-kui Yang, Chris Dickinson, and Ira Gantz

Novel Non-Phosphorylated Peptide Binding to the Grb2-SH2 DomainFeng-Di T. Lung, Lakshmi Sastry, Shaomeng Wang, Bih-Show Lou,Joseph J. Barchi, C. Richter King, and Peter P. Roller

A Endothelin-A/Lutropin Chimeric Receptor Exhibits Ligand-MediatedInternalization in the Absence of Signaling

Neil Bhowmick, Prema Narayan, and David Puett

Examination of the Role of TMH VII in Subtype-Selective Ligand BindingUsing Semi-Synthetic Muscarinic Receptors

Carol B. Fowler, Harry LeVine, and Henry I. Mosberg

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Modeling Somatostatin Receptor-Ligand ComplexesXiaohui Jiang and Murray Goodman

Session VII. Neuro-, Endocrino-, and Bioactive PeptidesSolution Synthesis and Structure Revision of Dendrotoxin I

Hideki Nishio, Tatsuya Inui, Yuji Nishiuchi, Edward G. Rowan, Alan L.Harvey, Terutoshi Kimura, and Shumpei Sakakibara

Amphipathic and Peptides with in Vitro and in VivoBioactivity

Mark L. McLaughlin, T. Scott Yokum, Ted J. Gauthier, Robert P.Hammer, and Philip H. Elzer

[D-Pen2,7]-human-α -Calcitonin Gene-Related Peptide: a NovelCGRP Antagonist

D. David Smith, Shankar Saha, David J.J. Waugh, and Peter W. Abel

Improved Parathyroid Hormone Analogue for the Treatment of OsteoporosisJ.-R. Barbier, V. Ross, P. Morley, J.F. Whitfield, and G.E. Willick

Multifunctional Chimeric Analogs of Small Peptide Hormones: Agonists andReceptor-Selective Antagonists

John Howl and Mark Wheatley

Generation of New Dmt-Tic Opioid Antagonists: N-AlkylationLawrence H. Lazarus, Severo Salvadori, Gianfranco Balboni, RemoGuerrini, Clementina Bianchi, Peter S. Cooper, and Sharon D. Bryant

Novel D-Amino Acid Hexapeptide Calmodulin Antagonists Identified fromSynthetic Combinatorial Libraries

Sylvie E. Blondelle, Ema Takahashi, Ed Brehm, Rosa Aligue, Richard A.Houghten, and Enrique Pérez-Payá

Pseudopeptides and Cyclic Peptides Analogues of Osteogenic GrowthPeptide (OGP): Synthesis and Biological Evaluation

Yuchen Chen, Itai Bab, Andras Muhlrad, Arye Shteyer, Marina Vidson,Zvi Greenberg, Dan Gazit, and Michael Chorev

A Cyclic Heptapeptide Mimics CD4 Domain 1 CC’ Loop and Inhibits CD4Biological Function

Takashi Satoh, James M. Aramini, Song Li, Thea M. Friedman, JiminGao, Andrea E. Edling, Robert Townsend, Ute Koch, Swati Choksi,Markus W. Germann, Robert Korngold, and Ziwei Huang

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Analogs of Main Autophosphorylation Site of PTK as Substrates forSyk and Src PTKs

Paolo Ruzza, Andrea Calderan, Barbara Biondi, Arianna Donella-Deana,Lorenzo A. Pinna, and Gianfranco Borin

Positively Charged Residues of Glucagon: Role in Glucagon ActionCecilia G. Unson, Cui-Rong Wu, Connie P. Cheung, and R.B. Merrifield

Synthesis and Activity of Proteolysis-Resistant GLP-1 AnalogsD.L. Smiley, R.D. Stucky, V.J. Chen, D.B. Flora, A. Kriauciunas, B.M.Hine, J.A. Hoffmann, W.T. Johnson, R.A.Owens, F.E. Yakubu-Madus, andR.D. DiMarchi

Homo-Oligomeric Opioid Analogues and Incorporation of 4-trans-Aminomethylcyclohexanecarboxylic Acid (Amcca)

DeAnna L. Wiegandt Long, Peg Davis, Frank Porreca, and Arno F.Spatola

Replacement at Positions 17, 18, and 21 of Glucagon Leads to Formation ofa New Salt Bridge and to an Increase in Binding Affinities

Dev Trivedi, Jung-Mo Ahn, Ying Lin, John L. Krstenansky, Stephen K.Burley, and Victor J. Hruby

Design and Synthesis of Novel GnRH-Endothelin ChimerasDror Yahalom, Yitzhak Koch, Nurit Ben-Aroya, and Mati Fridkin

Receptor Specificity of [2,3-Cyclopropane Amino Acids]-fMLP AnalogsHiroaki Kodama, Eiichi Hirano, Takahiro Yamaguchi, Satoshi Osada,Masaya Miyzaki, Ichiro Fujita, Sumio Miyazaki, and Michio Kondo

Synthesis of Short Analogs of Neuropeptide Y Specific for the Y2Receptor Using the TASP Concept

Eric Grouzmann, Alain Razaname, Gabriele Tuchscherer, MariaMartire, and Manfred Mutter

Interaction with Membranes of Peptides Related to the Fusogenic Region ofa Sperm-Egg Fusion Protein

Haruhiko Aoyagi, Miyuki Kimura, Takuro Niidome, TomomitsuHatakeyama, and Hisakazu Mihara

Elucidation of the Conformational Features within a Series of TetrapeptidesWhich Determine the Selective Recognition of Versus Opioid Receptors

Jeffrey C. Ho, Carol A. Mousigian, and Henry I. Mosberg

xxxi

611

613

615

617

619

621

623

625

627

629

xxxii

Structure Activity Relationship of NDF IsoformsT.J. Zamborelli, G.S. Elliot, S. Hara, D.L. Lacy, D.M. Lenz, N. Lu, S.K.Pakar, B. Ratzkin, J.E. Tarpley, J.S. Whoriskey, S.K. Yoshinaga, andJ.P. Mayer

Solid State Conformation of Constrained Somatostatin Analogues with HighPotency and Spectificity for the µ -Opioid Receptor

Judith L. Flippen-Anderson, Jeffrey R. Deschamps, Christi Moore,Clifford George, Victor J. Hruby, Wieslaw Kazmierski, and G. GreggBonner

Design, Synthesis and Biology Activity of Cyclic GHRP-6 AnaloguesKjeld Madsen, Peter H. Andersen, Birgit Sehested Hansen, NilsLangeland Johansen, and Henning Thøgersen

Systematic Lactam Scan of Yields Potent Agonists andAntagonists

L. Cervini, C. Donaldson, S. Koerber, W. Vale, and J. Rivier

The Interaction Between Gramicidin S and Lipid Bilayers: Evidence forCholesterol Attenuation of Phospholipid-Peptide Interactions

T.P.W. McMullen, E. J. Prenner, R.N.A.H. Lewis, L.H. Kondejewski,R.S. Hodges, and R.N. McElhaney

New Synthetic Peptides Derived from Human Fibroblast Growth Factor-1:Search for Agonists and Inhibitors

S. Kiyota, A.G. Gambarini, W. Viviani, S. Oyama, B.D. Sykes,and M.T.M. Miranda

Rapid Modular Total Chemical Synthesis of Chemokines Based on GenomeSequence Data

Michael A. Siani, Barren A. Thompson, Lynne E. Canne, Jill Wilken,Gianine M. Figliozzi, Stephen B.H. Kent, and Reyna J. Simon

Synthesis and Study of All-L and All-D Normal and Retro Isomers ofCecropin A-Melittin Hybrids and Selective Enzyme Inactivation

Satyanarayana Vunnam, Padmaja Juvvadi, Kenneth S. Rotondi, andR.B. Merrifield

Characterization of Neurokinin Receptor Types and Their Intracellular SignalTransduction in C1300 Cells

Shigetomo Fukuhara, Hidehito Mukai, and Eisuke Munekata

631

633

635

637

639

641

643

645

648

Influence of Different Types of Cyclization on Certain Biological Activitiesof Three Structural Types of Bradykinin Antagonists

Siegmund Reissmann, Inge Agricola, Torsten Steinmetzer, Lydia Seyfarth,Georg Greiner, and Inge Paegelow

Antimicrobial Peptides with Activity Against an Intracellular PathogenT.S. Yokum, P.H. Elzer, and M.L. McLaughlin

Properties of Cyclic Peptides Having Inhibitory Site of InhibitorTendamistat

Tomiya Hirano, Shin Ono, Hiroyuki Morita, Toshiaki Yoshimura, HirokiYasutake, Tetsuo Kato, and Choichiro Shimasaki

Solid-Phase Synthesis of Caged Peptides Containing Photolabile Derivativesof Aspartic Acid

Yoshiro Tatsu, Yasushi Shigeri, Shinji Sogabe, Noboru Yumoto, andSusumu Yoshikawa

Induction of Erectogenic Activity in the Human Male by Systemic deliveryof a Melanotropic Peptide

M. Hadley and V.J. Hruby

Design and Synthesis of Opioid Mimetics Containing Pyrazinone Ring andExamination of Their Opioid Receptor Binding Activity

Yoshio Okada, Masaki Tsukatani, Hiroaki Taguchi, Toshio Yokoi,Sharon D. Bryant, and Lawerence H. Lazarus

Intracellular Third Loop of Galanin Receptor as G-Protein Interaction SiteUrsel Soomets and Ülo Langel

Session VIII. Protease InhibitorsPotent Dipeptide HIV Protease Inhibitors Containing theHydroxymethylcarbonyl Isostere as an Ideal Transition-State Mimetic

Yoshiaki Kiso, Satoshi Yamaguchi, Hikaru Matsumoto, Tsutomu Mimoto,Ryohei Kato, Satoshi Nojima, Haruo Takaku, Tominaga Fukazawa,Tooru Kimura, and Kenichi Akaji

Rational Design and Synthesis of Conformationally Constrained Inhibitors ofHuman Cathepsin D

Pavel Majer, Jack R. Collins, Wenxi Pan, Sergei V. Gulnik, Angela Lee,Elena Gustchina, and John W. Erickson

xxxiii

650

652

654

656

658

660

662

667

670

xxxiv

Discovery of a Novel, Selective, and Orally Bioavailable Class of ThrombinInhibitors Incorporating Aminopyridyl Moieties at the P1 Position

Dong-Mei Feng, Roger M. Freidinger, S. Dale Lewis, Stephen J. Gardell,Mark G. Bock, Zhonggo Chen, Adel Naylor-Olsen, Richard Woltmann,Elizabeth P. Baskin, Joseph J. Lynch, Robert Lucas, Jules A. Shafer,Kimberley B. Dancheck, I- Wu Chen, and Joseph P. Vacca

Aminopeptidase A: Selective Inhibition and Physiological Involvement inMetabolism

Laurent Bischoff, Christelle David, Tarik Khaznadar, Valérie Daugé,Bernard Pierre Roques, and Marie-Claude Fournié-Zaluski

Synthetic Proregion-related Peptides of Proprotein Convertases, PC1 andFurin, Represent Potent Inhibitors of Each Protease

Ajoy Basak, Dany Gauthier, Nabil G. Seidah, and Claude Lazure

“O, N-Acyl Migration”-Type Prodrugs of Dipeptide HIV Protease InhibitorsYoshiaki Kiso, Satoshi Yamaguchi, Hikaru Matsumoto, Tooru Kimura,and Kenichi Akaji

The Crystal Structure of with Retro-Binding Inhibitor SEL2711Igor Mochalkin and Alexander Tulinsky

Novel Peptide Inhibitors for Processing in MonocytesSándor Bajusz, Irén Fauszt, Klára Németh, Éva Barabás, Attila Juhász,and Miklós Patthy

Synthetic Route to Suitable for Radiolabeling StudiesSusan Y. Tamura, J. Edward Semple, David C. Rowley, Paul McNamara,Ruth F. Nutt, and William C. Ripka

Peptide Vinyl Sulfones: Inhibitors and Active Site Probes for the Study ofProteasome Function In Vivo

Matthew Bogyo, John S. McMaster, Richard Glas, Maria Gaczynska,Domenico Tortorella, and Hidde L. Ploegh

Synthesis of 3-(3-Pyrrolidinyl)alanine and its Derivatives as ArgininePeptidomimetics for Incorporation into Serine Protease Inhibitors

Darin R. Kent, Wayne L. Cody, and Annette M. Doherty

Design of a Protein-Based Inhibitor for Proprotein Convertase Furin:Expression, Purification and Inhibition of Furin Substrates In Vivo by anEpitope-tag Recombinant Serpin

François Jean, Kori Stella, Craig J. Lipps, James B. Hicks, and GaryThomas

672

674

676

678

680

682

684

686

688

690

Session IX. Glyco-, Lipo-, and Phospho PeptidesMultiphosphorylated Synthetic Peptides as Antigens and Immunogens inAlzheimer’s Disease Paired Helical Filaments

Laszlo Otvos, Jr., Virginia M.-Y. Lee, Susan Leight, Peter Davies, and RalfHoffmann

Synthesis of Fluoroalkylated Muramyl Dipeptide Analogs withLipophilic Character

Zheng-Fu Wang and Jie-Cheng Xu

Lipoderivatives of an Immunodominant Epitope of Myelin Basic ProteinIncreased T Cell Responsiveness in Lewis Rats

Anna M. Papini, Silvia Mazzucco, Daniela Pinzani, Massimo Biondi,Mario Chelli, Mauro Ginanneschi, Gianfranco Rapi, Benedetta Mazzanti,Marco Vergelli, Luca Massacesi, and Luigi Amaducci

Antibacterial Insect Glycopeptides: Synthesis, Structure and ActivityLaszlo Otvos, Jr., Philippe Bulet, Istvan Varga, and Ralf Hoffmann

1997 ABRF Peptide Synthesis Research Committee Study on a PeptideContaining a Phosphorylated Tyrosine

Lynda F. Bonewald, Lisa Bibbs, Steven A. Kates, Ashok Khatri, KatalinF. Medzihradszky, John S. McMurray, and Susan T. Weintraub

Targeting a Hydrophobic Patch on the Surface of the Grb2-SH2 DomainLeads to High-Affinity Phosphotyrosine-Containing Peptide Ligands

H. Fretz, P. Furet, J. Schoepfer, C. Garcia-Echeverria, B. Gay, J. Rahuel,and G. Caravatti

Synthesis and Purification of Unphosphorylated and PhosphorylatedPhospholamban

Holger Schmid, Sjouke Hoving, Stefan Vetter, Thomas Vorherr, andErnesto Carafoli

Design and Synthesis of Controlled Oligomeric Neo-C-Glycopeptides asMultivalent Inhibitors of Carbohydrate-Protein Interactions

Johanne Roby, Robert N. Ben, Kristina Kutterer, Huiping Qin, GeorgeK.H. Shimizu, Michael Barnes, and Prabhat Arya

Structural Analysis of Peptide Substrates for O-GlycosylationL. Kirnarsky, O. Prakash, S.M. Vogen, Y. Ikematsu, N. JohnsonKaufman, S.D. Sanderson, H. Clausen, M.A. Hollingsworth, and S.Sherman

xxxv

695

698

700

703

705

707

709

711

713

xxxvi

Phosphopeptide Models of the C-Terminal Basic Domain of p53Ralf Hoffmann, Randall E. Bolger, Zhi Quan Xiang, Magdalena Blaszczyk-Thurin, Hildegund C.J. Ertl, and Laszlo Otvos, Jr.

Solid Phase Synthesis of N- and O-Glycopeptide by Boc-StrategyTadashi Teshima, Saeko Oikawa, Kumiko Y. Kumagaye, KiichiroNakajima, and Tetsuo Shiba

Novel Dde-Protected Glycoamino Acids and Glycoazido Acids inSaccharopeptide Synthesis

Gyula Dekany, Bruno Drouillat, Barrie Kellam, and Istvan Toth

Session X. Peptide BiologyDesign of Novel Melanotropin Antagonists and Agonists for the RecentlyDiscovered MC3, MC4 and MC5 Receptors and Their Use to DetermineNew Biological Roles

Victor J. Hruby, Guoxia Han, Wei Yuan, Sejin Lim, Carrie Haskell-Luevano, Roger D. Cone, Gergo Kunos, and Mac E. Hadley

Cellular Import of Founctional PeptidesJacek Hawiger

Novel Highly Potent Bradykinin Antagonists ContainingPentafluorophenylalanine

Lajos Gera and John M. Stewart

Application of Cell-Permeable Peptides to the Functional Analysis of EGF-Induced Mitogenic Signaling Pathways

Mauricio Rojas, SongYi Yao, John P. Donahue, and Yao-Zhong Lin

Biological Functions of Synthetic Peptides Derived from the Laminin Alpha 1Chain G Domain

Motoyoshi Nomizu, Yuichiro Kuratomi, Woo Ho Kim, Sang-Yong Song,Matthew P. Hoffman, Hynda K. Kleinman, and Yoshihiko Yamada

Competitive Antagonists of the Corticotropin Releasing Factor (CRF)Scanned with a i-(i+3) Glu Lys Bridge

A. Miranda, S. Lahrichi, J. Gulyas, C. Rivier, S. Koerber, C. Miller, A.Corrigan, S. Sutton, A. Craig, W. Vale, and J. Rivier

Cytocidal Effect of Custom Antibacterial Peptides on Leukemia Cancer CellsHueih Min Chen, Wei Wang, David Smith, and Siu-Chiu Chan

715

717

719

723

726

730

733

735

737

739

In Vitro and in Vivo Properties of NSL-9511, a Novel Anti-PlateletHexapeptide without an RGD Sequence

Jun Katada, Yoshio Hayashi, Yoshimi Sato, Michiko Muramatsu, YoshimiTakiguchi, Takeo Harada, Toshio Fujiyoshi, and Isao Uno

Model Peptides of Interstitial Collagens: Hydrolysis by MatrixMetalloproteinases

Kathleen Tuzinski, Ken-ichi Shimokawa, Hideaki Nagase, and GreggB. Fields

Serum Amyloid A and its Related Peptide Modulate Endothelial CellsProliferation and Prostaglandin Production

Liana Preciado-Patt, Ruth Shainkin-Kestenbaum, and Mati Fridkin

A New Paradigm for Fish Antifreeze Protein Binding to IceMichael Houston, Jr., Heman Chao, Michèle C. Loewen, Frank D.Sönnichsen, Cyril M. Kay, Brian D. Sykes, Peter L. Davies, and RobertS. Hodges

Neuropeptides and Skin Cell Function: VIP and Effectson HaCaT Cells

Ruth Granoth, Mati Fridkin, and Illana Gozes

Inhibiting Dimerization and DNA Binding of c-JunS.Q. Yao, E.I. Pares-Matos, M.L. Brickner, and J.A. Chmielewski

Inhibition of E-Cadherin-Mediated Cell-Cell Adhesion by Cadherin PeptidesK.L. Lutz, D. Pal, K.L. Audus, and T.J. Siahaan

Discovery and Structure-Activity Relationship Study of a Novel and SpecificPeptide Motif, Pro-X-X-X-Asp-X, for Platelet Fibrinogen ReceptorRecognition

Yoshio Hayashi, Jun Katada, Yoshimi Sato, Katsuhide Igarashi, TakeoHarada, Michiko Muramatsu, Emiko Yasuda, and Isao Uno

Session XI. Peptide Vaccines/Immunology/VirusesSynthetic Combinatorial Libraries for the Study of Molecular Mimicry:Identification of an All D-Amino Acid Peptide Recognized by an Anti-carbohydrate Antibody

Clemencia Pinilla, Jon R. Appel, Jaime Buencamino, Gretchen D.Campbell, Jutta Eichler, Neil S. Greenspan, and Richard A. Houghten

Processing of Peptide Antigens in EBV-Transformed B Cells and in an InVitro System

Hubert Kalbacher, Hermann Beck, Christian Schröter, Martin Deeg,Helmut E. Meyer, and Thomas Halder

xxxvii

741

743

745

747

749

751

753

755

761

763

xxxviii

New Ligands for MHC Molecules Based on Activity Patterns of PeptideLibraries

Karl-Heinz Wiesmüller, Burkhard Fleckenstein, Peter Walden, RolandMartin, and Günther Jung

Transformation of a L-Peptide Epitope into a D-Peptide AnalogAchim Kramer and Jens Schneider-Mergener

Production of Potent-Specific Antigens and Effective Immunogens UsingSequential Oligopeptide Carriers (SOCn)

Constantinos Sakarellos, Vassilios Tsikaris, Eugenia Panou-Pomonis,Charalampos Alexopoulos, Maria Sakarellos-Daitsiotis, ConstantinosPetrovas, Panagiotis G. Vlachoyiannopoulos, and Haralampos M.Moutsopoulos

Cross-Immunogenicity of Topological Mimics of Peptide AntigensMaria Rossi, Antonio Verdoliva, Menotti Ruvo, and Giorgio Fassina

Searching for Dominant Linear Antigenic Region of Hepatitis B SurfaceAntigen with Human Immune Sera Against Phage-Displayed RandomPeptide Library

Zhi-Jian Yao, Lay-Hain Ong, Lily Chan, and Maxey C.M. Chung

Comparative Immunological Properties of Lipidated HIV-1 gp41 Fragmentson Various Structural Templates

Artur Pedyczak, Dave McLeod, Olive James, Michel Klein, and PeleChong

Biological Effects of Peptide Antibodies Raised to HER-2/neu. Implicationsfor Therapy of Human Breast Cancer

Donna Woodbine, Naveen Dakappagari, Pierre Triozzi, VernonStevens, and Pravin T.P. Kaumaya

A Multiple Branch Peptide Construction Derived from a Conserved Sequenceof the Envelope Glycoprotein gp41 Inhibits Human Immunodeficiency VirusInfection

Jean-Marc Sabatier, Maxime Moulard, Emmanuel Fenouillet, HervéRochat, Jurphaas Van Rietschoten, and Kamel Mabrouk

Antigenic Domains of Shigella Virulence ProteinsKevin R. Turbyfill and Edwin V. Oaks

Characterization and Immune Response of a Novel Synthetic PeptideVaccine for HTLV-I

Melanie Frangione and Pravin T.P. Kaumaya

766

769

771

773

775

777

779

781

783

785

Mapping of the Immunodominant B- and T-Cell Epitopes of the OuterMembrane Protein D15 of H. influenzae Type b Using Overlapping SyntheticPeptides

Pele Chong, Olive James, Yan-Ping Yang, Charles Sia, Sheena Loosmore,Dave McLeod, and M. Klein

A Novel Bovine Antimicrobial Peptide of the Cathelicidin FamilyRenato Gennaro, Marco Scocchi, Laura Merluzzi, Shenglun Wang,and Margherita Zanetti

On the Reaction Kinetics of Peptide: Antibody Binding in the “BIAcoreTM”Biosensor

Robert M. Wohlhueter, Sunan Fang, Thomas W. Wells, and Danny L. Jue

V3-Mediated Neutralisation of Primary Isolates. Serology with SyntheticV3 Peptides Demonstrates Deficiencies in Anti-V3 Response

R. Pipkorn, A. Lawoko, B. Johansson, B. Christenson, B. Ljungberg,U. Dietrich, L. Alkhalili, E-M Fenyö, and J. Blomberg

Conformational Mapping of a Neutralizing Epitope on the C4 Region ofHIV-1 gp120 with Cyclic And Bicyclic Peptides

Ruoheng Zhang, Yuan Xu, Gerald R. Nakamura, Philip W. Berman, andArnold C. Satterthwait

Further Characterization of Anchor and Non-Anchor Residues on Deca- andUndeca-Peptides in Addition to Nona-Peptides, Which Bind to HLA Class IMolecules (HLA-B*3501)

Kiyoshi Nokihara, Christian Schönbach, and Masafumi Takiguchi

Delivery of Peptide Epitopes for HTLV-I Using Biodegradable MicrospheresMelanie Frangione, Travis Rose, Steven P. Schwendeman, Vernon C.Stevens, and Pravin T.P. Kaumaya

Session XII. Analytical MethodsDifferences in Encephalitogenicity in MBP Peptide 68-88 Due to HistidineRacemization

P.L. Jackson, M. Villain, F.S. Galin, N.R. Krishna, and J.E. Blalock

TFA/HCl Mixture as an Alternative to the Standard Propionic Acid/HClMixture for Aminoacyl- and Peptidyl-Resin Hydrolysis

G.N. Jubilut, A. Miranda, E. Oliveira, E.M. Cilli, M. Tominaga, andC.R. Nakaie

Investigation of Aggregation and Binding of Using NMRSpectroscopy

Dimuthu A. Jayawickrama and Cynthia K. Larive

xxxix

787

789

791

793

795

797

799

803

805

807

xl

ESI-MS and MALDI-MS Analysis, and Amino Acid Sequencing of ThreeMultiple-Antigen Peptides (MAPs)

Robert R. Becklin and Dominic M. Desiderio

Stability Studies on Peptide Aldehyde Enzyme InhibitorsPatricia A. Messina, John P. Mallamo, and Mohamed A. Iqbal

The Selectivity of C18 Reversed-Phase for Peptides Depends on the Type ofSilanes Linked to the Silica Matrix

Paul J. Kostel, Yan-Bo Yang, and William H. Campbell

Purification of a Crude Synthetic Peptide by Strong Cation Exchange:Breaking Up Hydrophobic Complexes Prior to Reversed-Phase

Paul Kostel

Molecular Recognition Using a Peptide Combinatorial Library and ItsDetection by Surface Plasmon Resonance Spectroscopy

Hiroshi Taniguchi, Koji Inai, Takahisa Taguchi, and Susumu Yoshikawa

Preliminary Mapping of Conformational Epitopes on the HPV-16 E7Oncoprotein

Julio C. Calvo, Katia C. Choconta, Diana Diaz, Oscar Orozco, FabiolaEspejo, Fanny Guzman, and Manuel E. Patarroyo

Session XIII. Drug DeliverySynthesis, Characterization and Use of Novel Non Viral Vectors for GeneDelivery

Gerardo Byk, Catherine Dubertret, Bertrand Schwartz, Marc Frederic,Gabrielle Jaslin, and Daniel Scherman

Prodrug Strategies to Enhance the Permeation of Peptides Through theIntestinal Mucosa

Ronald T. Borchardt

Characterization of a Stable Leuprolide Formulation for One Year in anImplantable Device

Cynthia L. Stevenson, Cynthia A. Corley, Matt Cukierski, Corinne A.Falender, Steven C. Hall, Paul Johnson, J. Joe Leonard, Mandy M. Tan,and Jeremy C. Wright

Oligopeptide Transport Systems in EukaryotesJeffrey M. Becker, Mark Lubkowitz, and Fred Naider

809

811

813

815

817

819

823

825

828

831

Brain Delivery and Targeting of Thyrotropin-Releasing Hormone Analogs byCovalent Packaging and Sequential Metabolism

Laszlo Prokai, Katalin Prokai-Tatrai, Wei-Mei Wu, Jiaxiang Wu, XudongOuyang, Ho-Seung Kim, Alevtina Zharikova, James Simpkins, andNicholas Bodor

A Novel Lipoamino Acid Based System for Delivery of Leu-Enkephalinamide Derivatives Through the Blood-Brain Barrier

Barrie Kellam, Mike S. Starr, Temitope G. Lamidi, and Istvan Toth

Hydrophobic Peptides: Synthesis and Interaction with Model MembranesFrancesca Reig, Isabel Haro, Patricia Sospedra, and M.Asunción Alsina

Importance of Hydrophobic Region in Cationic Peptides on Gene TransferNaoya Ohmori, Takuro Niidome, Taira Kiyota, Sannamu Lee, GohsukeSugihara, Akihiro Wada, Toshiya Hirayama, Tomomitsu Hatakeyama,and Haruhiko Aoyagi

A Novel Lipoamino Acid Based System for Peptide Delivery: Applicationfor Administering Tumour Selective Somatostatin Analogues

Nicholas S. Flinn, Judit Erchegyi, Aniko Horvath, Gyorgy Keri, andIstvan Toth

Aerosol Delivery of Peptide Immuno-Modulators to Rodent LungsRonald J. Pettis and Anthony J. Hickey

Indexes

Author Index

Subject Index

xli

834

837

839

841

843

845

847

861

Preface

The Fifteen American Peptide Symposium (15APS) was held in Nashville, Tennessee, on

June 14-19, 1997. This biennial meeting was jointly sponsored by the American Peptide Society

and Vanderbilt University. The attendance of 1,081 participants from 37 countries was lower

than the two previously held Symposia. However, the number of participating countries was the

largest. Thus, it was gratifying to see that this meeting retained both its international flavor and

participant loyalty at a time when there are many more symposia held each year on similar

subjects.

The scientific program, thanks to the insights and efforts of the Program Committee as

well as Dr. Peter Schiller, the President of the American Peptide Society, was extraordinarily rich,

diverse, and exciting. It was comprised of 124 oral and 550 poster presentations. Three

prominent format changes were installed. First, the Symposium started on Saturday instead of

Sunday. Second, the program opened on Saturday afternoon with a Mini-symposium by the

Young Investigators to give them an early start and attention. Finally, 40 short and definitive

reports were given in two parallel sessions. The expanded format permitted an unprecedented

number of lectures and enabled wider participation by the attending delegates.

Dr. Ralph Hirschmann, Makineni Professor of Bioorganic Chemistry at the University of

Pennsylvania, officially opened the Symposium on Sunday morning with an exciting lecture

entitled “’The time has come,’ the walrus said, ‘to talk of many things.’” His lecture focused on

past achievements and contributions of peptide chemistry and biology to science and health care.

Sessions I and II covered the frontiers and novel concepts of peptide science. Sessions III

to VI dealt with the problems in minimizing proteins to peptides and peptides to drugs.

xliii

xliv

Sessions VII, VIII and XIX dealt with the increasing importance of peptide mimetics and

diversity, including combinatorial libraries, in drug design. Specific problems of peptide and drug

designs were also addressed in sessions IV and XX. The problems of drug delivery were explored

in Session XVIII.

Other sessions dealt with protein folding, receptor-ligand interactions, peptide biology,

peptide immunology and conformational analysis.

This symposium marked the first official presentation of the Merrifield Award, newly

endowed by Dr. Rao Makineni. The Alan E. Pierce Award was discontinued. The Merrifield

Award recognizes outstanding contributions to the chemistry and biology of peptides and

represents the most prestigious award given by the American Peptide Society. This year’s

recipient was Dr. Shumpei Sakakibara of the Peptide Institute, Inc., Protein Research Foundation,

Japan. Dr. Sakakibara delivered the Makineni lecture entitled “Fifty Years of My Protein

Synthesis” in which he succinctly described his experience in the arts and methods of protein

synthesis.

The success of the APS was largely due to the dedication, enthusiasm and hard work

of the local organizing committee, who for the most part consisted of volunteers. As Symposium

Chair, I am deeply indebted to the postdoctoral fellows in my laboratory at Vanderbilt University.

They worked tirelessly, often past midnight, to meet deadlines, and there were many such

deadlines. They each spent nearly two months of their time correcting, collating, typing, editing,

and proofreading all printed materials, including this proceeding volume. I am also indebted to

Ms. Vicki Bryant, my secretary, for her patience in handling adminstrative matters. Most of all, I

am forever grateful to my wife, Sylvaine who shouldered the enormous task of creating the

symposium database, keeping track of the correspondence, abstracts, registrations, and

xlv

manuscripts as well as maintaining the book-keeping on financial matters and audits.

We are especially grateful for the generous financial support by the Benefactors, Sponsors,

Donors and Contributors who are listed on the following pages. Their support enabled the

excellence expected of this meeting. Special thanks goes to Polypeptide, Inc. for providing the

funds for the purchase of the symposium bags. The Chairman would also like to acknowledge the

Department of Microbiology and Immunology, particularly its chairman, Dr. Jacek Hawiger. I

also thank Vanderbilt University for their support for holding the 15th American Peptide

Symposium in Nashville.

Finally, I would like to acknowledge Ms. Victoria Shaw and her band for their wonderful

performance at the closing banquet and for providing a fond memory for all APS attendees.

James P. Tam

Pravin T.P. Kaumaya

June 14-19, 1997

Chairman - James P. Tam, Vanderbilt University

PROGRAM COMMITTEE MEMBERS

George Barany University of MinnesotaRichard DiMarchi Eli Lilly & CompanyAnnette Doherty Park-DavisGregg B. Fields University of MinnesotaRoger M. Freidinger Merck, Sharp & DohmeMurray Goodman University of CaliforniaJacek Hawiger Vanderbilt UniversityWilliam Heath Eli Lilly & CompanyRichard A. Houghten Torrey Pines InstituteIsabelle Karle Naval Research CenterGarland R. Marshall University of WashingtonJohn P. Mayer Amgen, Inc.Daniel Rich University of WisconsinArno Spatola University of LouisvilleJames A. Well Genetech, Inc.

AMERICAN PEPTIDE SOCIETY

Officers

Peter W. Schiller President Clinical Research Inst. of

Montreal

Robert S. Hodges President-Elect University of Alberta

Ruth F. Nutt Secretary

Teresa M. Kubiak Treasurer Pharmacia & Upjohn, Inc.

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xlvii

CouncilorsGeorge Barany Lila M. Gierasch Tomi K. SawyerDavid H. Coy Richard A. Houghten James P. TamRichard D.DiMarchi Kenneth D. Kopple Daniel F. VeberWilliam F. DeGrado Daniel H. Rich Janis D. Young

Honorary MembersElkan R.Blout Ralph F. Hirschmann Andrew V. SchallyMiklos Bodanszky Victor J. Hruby Harold A. ScheragaGerald D. Fasman Isabella L. Karle Robert SchwyzerJoseph S. Fruton Rao Makineni John M. StewartMurray Goodman Bruce R. Merrifleld Daniel F. VeberRoger Guillemin Shumpei Sakakibara

Local Planning Committee

James P. Tarn ChairVicki Bryant Symposium SecretaryTraci Castleman RegistrationFaith Chan RegistrationPrzemyslaw Cieszynski Operational ManagerJohn Donahue Transportation CoordinatorChristophe Hennard Hospitality CommitteeA. Kasia Jarzecka RegistrationKalle Kaljuste Vanderbilt Accommodation's CoordinatorAlan Kilpatrick Computer Applications ConsultantYao-Zhong Lin Hospitality CoordinatorYi-An Lu Hospitality CommitteeDale McClendon Exhibit AssistantSteven Muhle Hospitality CommitteeGosia Pawlak RegistrationSue Rowlinson RegistrationGreta Tam RegistrationJonathan Tam RegistrationSylvaine Tam Data ManagerSheila Timmons Hotel Accommodations CoordinatorCarol Water Manuscript EditorDeborah West RegistrationOla Wyslouch-Cieszynska Abstract/Program Book CoordinatorQitao Yu Audio Visual CoordinatorLianshan Zhang Child Care/AV Coordinator

ACKNOWLEDGMENTS

The Fifteenth American Peptide Symposium organizing committee is grateful for thefinancial and administrative support of the host institution:

VANDERBILT UNIVERSITY

Medical School, Department of Microbiology & ImmunologyThe Fifteenth American Peptide Symposium organizing committee also greatly appreciatesthe support and generous financial assistance of the following organizations:

BENEFACTORS

PolyPeptide Laboratories GroupPolyPeptide Laboratories, Inc., USA

PolyPeptide Laboratories AB, Sweden

PolyPeptide Laboratories A/S, Denmark

SPONSORS

Hoffman-LaRoche

Amgen

C S Bio Co.

Eli Lily & Company

Genzyme Pharmaceuticals

Synthetech

Abbott Laboratories

Mallinckrodt Chemicalxlviii

DONORS

Pfizer

Bio-SynthesisBiomeasure

Multiple Peptide Systems

Peninsula Laboratories

SmithKline BeechamUCB-Bioproducts S. A.

Biogen

Glaxo Wellcome

Merck Research LaboratoriesNeuropeptide Dynamics

Orpegen PharmaParke-Davis Pharmaceutical Research

Pharmacia & Upjohn

CONTRIBUTORS

AlzaBio-Mega

Bristol-Myers SquibbDupont-Merck

WatersZeneca Pharmacetuticals

Sigma-Aldrichxlix

The Merrifield Award 1997

(Generously endowed by Dr. Rao Makineni)

Shumpei Sakakibara

The first recipient of the newly created Merrifield Award is Dr. ShumpeiSakakibara, founder and long-time chairman of Peptide Institute Inc., Protein ResearchFoundation, Osaka, Japan. This award has recently been created through the effort of Dr.James P. Tam and with a generous endowment from Dr. Rao Makineni who retired fromBachem California last year. The Merrifield Award represents the most prestigious APSaward and continues under a new title the Society’s previous Alan E. Pierce Award.

Dr. Sakakibara is one of the world’s foremost leaders in peptide chemistry. One ofhis major scientific contributions was the development of the hydrogen fluoride cleavagereaction in solid-phase peptide synthesis. Another great achievement of his illustriouscareer is the synthesis, by solid-phase or fragment condensation methods, of large,complex biologically active peptides, including human parathyroid hormone-(l-84),omega-conotoxin GIVA, omega-agatoxin IVA, porcine C5a anaphylatoxin, angiogenin-(1-123), calciseptine and human midkine.

Dr. Sakakibara started his career as research associate in the laboratory of ProfessorShiro Akabori at Osaka University (1951-60) and received his Ph. D degree from the sameuniversity. He was a research associate at Cornell University, Ithaca (1960-63). He thenreturned to Japan to assume a position as associate professor in the Institute for ProteinResearch at Osaka University. In 1971, he founded the Peptides Institute (Protein ResearchFoundation) in Osaka and served as its director (1971-76), president (1976-91) andChairman of the Board (1991-96). From 1990-1992, he was the president of the JapanesePeptide Society. His other awards include the Chemical Technology Award from the KinkiChemical Company, the Scoffone Medal, and the Hirschmann Award. Dr. Sakakibara isthe second non-American recipient of the American Peptide Society’s most prestigiousaward.

l

Alan E. Pierce Award

(Sponsored by Pierce Chemical Company, 1977-1995)

The recipient is an individual who has made outstanding contributions to techniques andmethodology in the chemistry of amino acids, peptides and proteins.

1995

1991

1987

1983

1979

John M. Stewart

Daniel VeberChoh Hao LiRalph Hirschmann

Bruce Merrifield

1993

1989

1985

1981

1977

Victor J. Hruby

Murray GoodmanRobert SchwyzerKlaus Hofmann

Miklos Bodanszky

American Peptide Symposia

Symposium

First 1968

Second 1970

Third 1972

Fourth 1975

Fifth 1977

Chair(s)

Saul LandeYale UniversityBoris WeinsteinUniversity of Washington, Seattle

F. Merlin BumpusCleveland Clinic, Cleveland

Johannes MeienhoferHarvard Medical SchoolBoston

Roderich WalterUniversity of IllinoisMedical Center, Chicago

Murray GoodmanUniversity of California-San Diego

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Location

Yale UniversityNew Haven, CTUSA

Cleveland ClinicCleveland, OH, USA

Children’s CancerResearch FoundationBoston, MA, USA

The Rockefeller Universityand Barbizon Plaza HotelNew York, NY, USA

University of California-San Diego, San Diego, CAUSA

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Sixth 1979

Seventh 1981

Eighth 1983

Ninth 1985

Tenth 1987

Eleventh 1989

Twelfth 1991

Thirteenth 1993

Fourteenth 1995

Fifteenth 1997

Sixteenth 1999

Erhard GrossNational Institute of HealthBethesda

Daniel H. RichUniversity of WisconsinMadison

Victor J. HrubyUniversity of ArizonaTucson

Kenneth D. KoppleIllinois Institute of TechnologyChicagoCharles M. DeberUniversity of Toronto, Toronto

Garland R. MarshallWashington UniversitySchool of Medicine, St. Louis

Jean E. RivierThe Salk Institute forBiological Studies, La Jolla

John A. SmithMassachusetts GeneralHospital, Boston

Robert S. HodgesUniversity of Alberta,Edmonton

Pravin T.P. KaumayaOhio State University,Columbus

James P. TamVanderbilt University MedicalSchool, Nashville

George Barany & Gregg FieldsUniversity of Minnesota,

Georgetown UniversityWashington, DC, USA

University of Wisconsin-Madison, Madison, WI.USA

University of ArizonaTucson, AZ, USA

University of TorontoToronto, OntarioCanada

Washington UniversitySt. Louis, MO, USA

University of California-San Diego, CA, USA

Massachusetts Institute ofTechnology, Cambridge,MA, USA

Edmonton ConventionCentre, Edmonton,Alberta, Canada

Ohio State UniversityColumbus, OH, USA

Nashville ConventionCenter, Nashville, TN,USA

Minneapolis, MN, USA

Seventeenth 2001 Richard A. HoughtenTorrey Pines Institute

San Diego, CA, USA

1997 Young InvestigatorS Poster CompetitionAwards

Harald K. Rau

Xiaohui JiangLi-Ping Liu

Ioana AnnisCarrie Haskell-LuevanoMatthew J. SandeholmCheryl A. SlateLukas C. Scheibler

Matthew BogyoMargaret L. FalconeMelanie FrangioneCarol B. FowlerWenli MaMichael RandallMichael D. SchultzSandra C. Vigil-Cruz

First Place

Albert-Ludwigs Universitat, Germanay

Second Place

University of California - San DiegoHospital for Sick Children andUniversity of Tonoton, Canada

Third Place

University of MinnesotaUniversity of MichiganUniversity of North Carolina, Chapel HillUniversity of North Carolina, Chapel HillUniversity of Lausanne, Switzerland

Honorable Mentions

Massachusetts Institute of TechnologyUniversity of MarylandOhio State UniversityUniversity of MichiganUniversity of MichiganOhio State UniversityPurdue UniversityUniversity of Maryland, Baltimore

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Poster Competition Judges

Jane Aldrich (Chair, Student Affairs Committee)Art Felix (Co-chair, Student Affairs Committee)Fernando Albericio Michael Chorev Wayne CodyBen Dunn Gregg Fields Deborah Heyl-CleggRichard Houghton Rodney Johnson Steve KatesLenore Martin Tom Muir Kerry SpearJohn Taylor Janis Young

American Peptide Society15th American Peptide Symposium Travel Grant Recipients

Jung-Mo Ahn, USALudmila Gennadyevna Alekseeva, RussiaLorenzo Josue Alfaro-Lopez, USAYvonne M. Angell, USAIoana Annis, USAJordi Bacardit, SpainBari A. Barwis, USAEric Beausoleil, CanadaVered Behar, USAMarta Del Rosario Benites, USAAlessandro Bisello, USABarney M. Bishop, USAGal Bitan, USAMatthew S. Bogyo, USAMichelle L. Brickner, USALin Chen, USAGuzin Dogruyol, USAAmanda L. Doherty-Kirby, CanadaMargaret L. Falcone, USAHong Fan, USATed J. Gauthier, USARuth Granoth, IsrealKaren S. Gregson, USAChristopher M. Gross, USAGuoxia Han, USAYinglin Han, USABalazs Hargittai, USABernd Henkel, GermanyHoebert S. Hiemstra, The Netherlands

Kristin Jauch, GermanFrancois Jean, USAXiaohui Jiang, USAMichael B. Keller, SwitzerlandWayne D. Kohn, Canada Jennifer A.Kowalski, USAHaitao Li, USASubo Liao, USAInta Liepina, LatviaAmareth Lim, USALi-Ping Liu, CanadaRalph-Heiko Mattern, USAKristofer K. Moffett, USABassam M. Nakhle, USASvetlana S. Pantchcva, BulgariaMaria M. Pellegrini, USALiana Preciado-Patt, IsrealMarketa Rinnova, Czech RepublicJohanne Roby, CanadaJaimie K. Rueter, USASheila D. Rushing, USAMatthew J. Saderholm, USASeiji Sakamoto, JapanMohamed D. Salamoun, USALukas C. Scheibler, SwitzerlandCheryl A. Slate, USATsuyoshi Takahashi, JapanYuta Takahashi, JapanAndreas Tholey, Japan

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Kin-ya Tomizaki, JapanShawn M. Vogen, USAQiang Wan, USAKevin R. Wyckoff, USAChristopher L. Wysong, USAQinghong Xu, USADror Yahalom, IsrealThomas Scott Yokum, USAChongxi Yu, USANatalya I. Zaitseva, Russia

Abbreviations

Abbreviations of common amino acids and units of measurements based on the IUPACnomenclature are not enumerated. However, other abbreviations used in this proceedingsvolume are defined below:

Abc

Abh

AblAbuAbz

ACAc

Aca

Acc

AEDI

AHAAhp

Ahx

AibAIIA1AllocAMama

hydrophobic momentmean residue ellipticity4’-aminomethyl-2,2’ -bipyridine-4-carboxylic acidazabicylco[2.2. l]heptane-2-carboxylic acidabelson kinase

2-amino-benzoic acid;2-aminobenzoyladenylylcyclaseacetyl; acyl1-amino-cyclohexyl-1-carboxylic acidadamantanecarboxyl-1-aminocyclopropane-1-carboxylic acidacetamidomethylaminoethyldithio-2-isobutyric acid6-aminohexanoic acid2-amino-heptanoic acid6-dehydro-2-amino-heptanoic acid6-aminohexanoic acidaminohexanoic acid

angiotensin IIallylallyloxycarbonylalveolar macrophageAc-Abc-Ahx-Orn(Mbc-

AMBER assisted model building andenergy refinement

AMC aminomethylcoumarideAMCA 7-amino-4-methylcoumarin-

3-acetic acidAmn 8-(aminomethyl)naphth-2-

oic acidAPB (4-amino)phenylazobenzoic

acidAPC antigen presenting cellApn 5-aminopentanoc acidArg-al argininalArg-ol argininolATP adenosine triphosphateAUC area under the curveAVP vasopressinBBAL backbone amide linker;

broncho-alveolar lavagebApG N,N-bis(3-aminopropyl)-

glycineBBB blood brain barrierBK bradykininBMAP bovine myeloid

antimicrobial peptideBMEBn benzylBoc, BOC tert-butyloxycarbonyl

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Acm

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Boc-ON

BOP

BpaBPTI

bpyBzlCaMCAMM

CBACbz

CCKCCK-BCD

CED3

CFCFUChaChgChoClt-resinCl-TrtCl-ZCpg

CRF

CTLd.e.DaDAMGO

2-tert-butyloxy-carbonylamino-2-phenylacetonitriledi-tertbutyl dicarbonate(benzotriazol-1 -yloxy)-tris(dimethylamino)phosphoniumhexafluorophosphatep-benzoylphenylalaninebovine Pancreatic trypsininhibitor2,2’-bipyridinebenzylcalmodulincomputer assisted molecularmodelingcarboxymethylcarbobenzoxy;benzyloxycarbonylcholecystokinincholecystokinin-Bcircular dichroism

cenorhabditis elegans cell-death protein5(6)-carboxyfluoresceincolony forming unitscyclohexylalanine

cholesteryl2-chlorotrityl resin2-Cl-trityl2-chlorobenzyloxycarbonyl

pseudo Cpg-Argcorticotropin releasingfactorcytotoxic T-lymphocytediastereomeric excessDalton

DB[DMAP]

DBU

DCCI; DCCDCMDde

Ddz

DHTDICDIEA

DIPCDI

DMAPDMER-Plot

DMFDMSODNPDOF-COSYCOSYDOPC

DOPG

DPCDPDPE

DPPADPPC

DPPG

DTTEAE

EBPproteinEBV

2,6-di-tert-butyl-4-(dimethylamino)pyridine1,8-diazabicyclo [5.4.0]-undec-7-enedicyclohexylcarbodimidedichloromethane1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl

dimethoxybenzyloxycarbonyl1,4-DihydrotrigonellyldiisopropylcarbodiimideMN-diisopropylethylamine;N-diisopropylethylamineN,N’-diisopropylcarbodiimide4-dimethylaminopyridinedifference minimum energyramachandran plotdimethylformamidedimethyl sulfoxidedinitrophenyldouble quantum field

phosphatidylcholine

phosphatidylgltceroldodecyl phosphocholine

diphenylphos-phorylazide

phosphatidylcholine

phosphatidylgltceroldithiothreitolexperimental allergicencephalomyelitiserytropoietin binding

Epstein-Barr virus

lviii

ED50 median effective doseEDT 1,2-ethanedithiolEDTA ethylenediamine-tetraacetic

acidEGF epidermal growth factorEGFR EGF receptorEGS ethylene glycol bis-succinyl-ELISA enzyme linked

immunosorbance assayEMP erytropoietin mimetic

proteinEPO erytropoietinES-MS electrospray mass

spectrometryESI electrospray ionizationESR electron spin resonanceESTs expressed sequence tagsET-1 endothelin-1

triethylamineendothelin-A receptordifluorophosphonomethylphenylalanine

f5f pentafluorophenylalanineFAB-MS fast atom bombardment

mass spectrometryFceRI IgE-receptor

FITC fluorescein isothiocyanatefMLP formyl-Met-Leu-PheFmoc; FMOC 9-fluorenylmethoxycarbonylFmoc-Cl 9-fluorenylmethoxy

chloroformateFTIR Fourier transform infraredGalR galanin receptorGdnHCl guanidinium hydrochlorideGFC gel filtration

chromatographyGlcNAc N-acetylgalactosamineGPCR G-protein-coupled receptorGpIIb/IIIa glycoprotein IIb/IIIa

growth factor receptor-

GRF

GSGSHGSSGGuHClHHat

HATU

HBTU

HBVhCGHCVHDAgHDVHFIPHGHIV

HLAhmhm 1 trune

HMCHMPA

HMPAHMPB

HOAt

bound protein 2growth hormone releasingfactorgramicidin Sreduced glutathioneoxidized glutathioneguanidine hydrochloridehydrophobicity2-amino-6-hydroxytetralin-2-carboxylic acidO-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluroniumhexafluorophosphate2-(lH-benzotriazol-1 -yl)-1,1,3,3-teramethyoluroniumhexafluorophosphatehepatitis B virushuman choriogonadotropinhepatitis C virushepatitis delta antigenhepatitis delta virushexafluoroisopropanolhuman gastrinhuman immunodeficiencyvirushuman leukocyte antigenhuman muscarinic receptortruncated muscarinicreceptorhydroxymethylcarbonylp-hydroxymethylphenoxyacetic acidhexamethylphosphoramide4-(4-hydroxymethyl-3-methoxyphenoxy)-butyricacidprotein nuclear magneticresonancetritiated N-methylscopalamine1-hydroxy-7-azabenzotriazole

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HOBtHPLC

HppHPVHSBOtU

HSBtU1-

HSF

HSNPtU

HSDNPtU

HTLVvirusInogatran

i.v.IAPPiBoc

ICE

IFN

Igl

1- hydroxybenzotriazolehigh performance liquidchromatography3-(4-hydroxyphenyl)prolinehuman papilloma virus(2-mercaptobenzoxazol-2-yl)-l,l,3,3-tetramethyluronium-hexafluorophosphate2-(1 -mercaptobenzoxazol-

yl)-1,1,3,3-tetramethyluronium-hexafluorophosphatehematopoietic synergisticfactor2-(l-mercapto-4-nitrophenyl-1-yl)-1,1,3,3-tetramethyluronium-hexafluorophosphate2-(l-mercapto-2,4-dinitrophenyl-1 -yl)-1,1,3,3-tetramethyluronium-hexafluorophosphatehuman T cell leukemia

glycine,N-{2-[2-[[[3- t(aminoiminomethyl)amino]propyl]amino]-carbonyl]-1-piperidinyl] 1 -(cyclohexylmethyl)-2-oxoethyl]-[2R-[25]]intravenousislet amyloid polypeptideisobutyloxycarbonyl50% inhibitionconcentrationinterleukin- convertingenzymeinterferon

inositol trisphosphate;1,4,5-

trisphosphateHC isothermal titration

calorimeryLAH lithium aluminum hydrideLDL low density lipoproteiLHR lutropin receptorLol leucinolLPS lipopolysaccharideLUV large unilamellar vesicleMAb monoclonal antibodyMAdCAM-1 mucosal addressin cell

adhesion molecule-1MALDI matrix-assisted laser

desorption/ionizationMALDI-MS MALDI

mass spectrometryMALDI-TOF MALDI time-of-MS flight mass spectrometryMAP mitogen-activated protein;

multiple antigen peptideMbc 4’-methyl-2,2’-bipyridine-4-

carboxylic acidMBHA para-

methylbenzhydrylamineMBHA

methylbenzhydrylamineMBP myelin basic proteinMC1R melanocortin-1 receptorMCR melanocortin receptorMD molecular dynamicsMDP muramyl dipeptideMe methylMeCN acetonitrileMeOBzl para-methoxybenzylMeOH methanolMER-Plot minimum energy

ramachandran plotMHC major histocompatibility

complexMIC minimum inhibitory

concentration

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MIF

MMPMmtMSMSH

MT-IMT-H

Mtr

MttNADPH

NalNc7gNchgNecNipNIR-FT

NK-1

NKANKBNKR cellsNMePhe;NMFNMMNMPNMRNOnOctNOENOESY

NPY

macrophage migrationinhibitory factormatrix metalloproteinase4-methoxytritylmass spectrometrymelanocyte stimulatinghormone, melanotropin

2,3,6-trimethyl-4-methoxybenzenesulfonyl4-methyltritylnicotinamide adeninedinucleotide phosphate,reduced formnaphthylalanineN-cycloheptylglycineN-cyclohexylglycinenorecgonidinenipecotic acidnear-infrared, fourier-transformneurokinin -1 receptor(substance P receptor)neurokinin Aneurokinin Bnormal rat kidney cells

N-methyl phenylalanineN-methylmorpholineN-methylpyrrolidinonenuclear magnetic resonancenitric oxiden-octanoylnuclear overhauser effectnuclear overhauserenhanced spectroscopyNeuropeptide Y

o-AMPA

OchxOHAOic

OmeOMIOPTOrnOrn-olOVXPAL

PAMamidating

PBMC

PBSPCPCRPd/CPDIPEGPEG-PS

PEGA

acid

acidnortropane-3-carboxylicacid

defined sequence position inpeptide librariesthe complete set of 220sublibrarieso-aminomethylphenylaceticacidcyclohexyl esteroctahydroacridineoctahydroindole-2-carboxylic acidmethoxyoxomorphindoleoligopeptide transportornithineornithinolovariectomytris(alkoxy)benzylamide;peptide amide linker, 5-(4-Fmoc-ainomethyl-3,5-dimethoxyphenoxy)valericacidpeptidyl glycine

monooxygenaseperipheral bloodmononuclear cellsphosphate-buffered salinephosphatidylcholinepolymerase chain reactionpalladium on carbonprotein disulfide isomerasepolyethylene glycolPolyethylene glycol-polystyrenepolyethylene glycol pole-

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acrylamide copolymerPen penicillaminePfp pentafluorophenyl esterPhe phenylalanine

4-

hydroxymethylphenylalaninePhe(4-Et) 4-ethylphenylalanine

dehydrophenylalanine;dehydrophenylalaninecyclopropylphenylalanine

PI phospatidylinositolPLC phospholipase CPLN phospholambanPLP proteolipid proteinPM plasma membranesPmc 2,2,5,7,8-

pentamethylchroman-6-sulfonyl

PMD Pelizaeus-Merzbacherdisease

pNA p-nitroanalinePnc

carboxylic acidpNpys 5-nitro-2-pyridinesulfenylPPCE post-proline cleaving

enzymePS polystyrenePSD/CID post source decay/collision-

induced dissociationPS-SCL positional scanning SCLPTH parathyroid hormonePTHrP parathyroid hormone related

proteinPTK protein tyrosine kinasePTP protein-tyrosine

phosphatasePTR peptide transportpTyr phosphotyrosinepY phosphotyrosine

PyAOP (7-azabenzotriazol-l-yloxy)-

tris(pyrrolidino)phosphoniumhexafluorophosphate

PyBOP (benzotriazol-1-yloxy)-tris(pyrrolidino)phosphoniumhexafluorophosphate

QSAR quantitative structure-activity relationships

relC relative competitionRGD Arg-Gly-AspRMSD root mean square deviationRNA ribonucleic acidRP reversed-phaseRP-HPLC reversed-phase high

performance liquidchromatographydichloro tetrakis(dimethylsulfoxide)ruthenium(II)ruthenium(II)ama complexed with

SAPS sequence assisted peptidesynthesis

SAR structure activityrelationships

SCLs synthetic combinatoriallibraries

SD standard deviationSH(32) dual domains with SH2 and

SH3SH2 src homology domain 2SH3 src homology domain 3SHU-9119

SNC-80allyl-2,5-dimethyl-l-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide

SIOM 7-spiroindoyloxymorphone

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SPSPPSsynthesisSPR

ATPasess-DNASub

SUVSynJ

TAN-67

TASP

TBDMS

TCEPTeaTEMPTFATFETFFH

TFMSA

THFThiTHPTic

TIP3P

substance Psolid phase peptide

surface plasma resonancesarcoplasmic reticulum

ATPasesingle-stranded DNA(2S,7S)-2,7 diaminosubericacidsmall unilamellar vesiclesynthetic J protein

hydroxyphenyl)-l,2,3,4,4a,5,12,12aoctahydroquinolino[2,3,3-g]isoquinolinetemplate-assembledsynthetic protein(s)tert-butyldimethylsilyltert-butyltris(carboxyethyl)phosphinetriethylamine2,3,5,6-tetramethylpyridinetrifluoroacetic acidtrifluoroethanoltetramethylfluoro-formamidiniumhexafluorophosphatetrifluoromethylsulfonic acidtransforming growth factoralphatetrahydrofuran

triple-helical peptide1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidtransferable inter-molecular

TLCTMHTmobTMPTMS-C1TMSITMT

TOAC

TOCSY

TosTPTU

TRH

Tris

TrtTsOH

W13

X

XAL

XanZ

potential 3 point waterthin layer chromatographytransmembrane helixS-2,4,6-trimethoxybenzyl2,4,6-trimethylpyridinetrimethylsilyl chlorideiodotrimethylsilane

dimethyltyrosine2,2,6,6-tetramethylpiperidine-1-oxyyl-4-amino-4-carboxylic acidtotal correlationspectroscopyp-toluenesulfonyl2-(2-oxo-l(2H)-pyridyl)-1,1,3,3-tetramethyluroniumtetrafluorophosphate;2-(2-pyridon-l-yl))-1,1,3,3-tetramethyluroniumfluoroboratethyrotropin-releasinghormonetris(hydroxymethyl)aminomethanetrityltoluenesulfonic acid3-nitrotyrosineN-(4-aminobutyl)-5-chloro-2-naphthalenesulfonamiderandomized sequenceposition in peptide libraries5-(9-aminoxanthen-2-oxy)valeric acidS-9H-xanthen-9-ylbenzyloxycarbonyl