Carbohydrate Biotechnology Protocols

M E T H O D S I N B I O T E C H N O L O G Y T M

John M. Walker, Se,~tEs EDITOR

12. Environmental Monitoring of Bacteria, edited by Clive Edwards, 1999 11. Aqueous Two-Phase Systems, edited by Rajni Hatti-Kaul, 1999 10. Carbohydrate Biotechnology Protocols, edited by Christopher Bucke, 1999 9. Downstream Processing Methods, edited by Mohamed Desai, 1999 8. Animal Cell Biotechnology, edited by Nigel Jenkins, 1999 7. Affinity Biosensors: Techniques and Protocols, edited by Kim R. Rogers

and Ashok Mulchandani, 1998 6. Enzyme and Microbial Biosensors: Techniques and Protocols, edited by

Ashok Mulchandani and Kim R. Rogers, 1998 5. Biopesticides: Use and Delivery, edited by Franklin R. Hall and Julius J. Menn, 1998 4. Natural Products Isolation, edited by Richard J. P. CannelL 1998 3. Recombinant Proteins from Plants: Production and Isolation of Clinically Useful

Compounds, edited by Charles Cunningham and Andrew J. R. Porter, 1998 2. Bioremediation Protocols, edited by David Sheehan, 1997 1. Immobilization of Enzymes and Cells, edited by Gordon F. Bickerstaff, 1997

Carbohydrate Biotechnology

Protocols

Edited by

Christopher Bucke School of Biosciences,

University of Westminster, London, UK

Humana Press ~(E Totowa, New Jersey

© 1999 Humana Press Inc. 999 Riverview Drive, Suite 208 Totowa, New Jersey 07512

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Methods in biotechnology TM.

Carbohydrate biotechnology protocols / edited by Christopher Bucke. p. cm.- - (Methods in biotechnology ; 10)

Includes index. ISBN 0-89603-563-8 (alk. paper) 1. Carbohydrates----Biotechnology--Laboratory Manuals. I. Bucke, C.

II. Series. TP248.65.P64C37 1999 660.6' %~:1c21 98-48663

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Preface

We are in a phase of the evolution of biotechnology in which the true and potential commercial importance of carbohydrates is becoming appreci- ated more fully. Progress in providing hard facts to establish the commercial value ofpolysaccharides and oligosaccharides is limited, as always, by lack of funding and by a relative shortage of skilled practitioners in the production and analysis of those materials. Carbohydrate science has a reputation, not unmerited, for technical difficulty owing to the structural similarity of the many monosaccharide monomers and the potential, and real, complexity of oligosaccharides and polysaccharides, particularly heterosaccharides contain- ing many different monomers. Modem analytical and synthetic methods, in many cases using enzyme technology, are beginning to allow this complexity to be unraveled.

Carbohydrate Biotechnology Protocols is aimed at those newcomers who have an interest in the production and use of carbohydrate materials, but have shied away from involvement for lack of detailed descriptions of appropriate methods, including the type of practical hints that may be provided by those skilled in those methods, but that are rarely described in research papers. The majority of the contributions to this book conform to the established format of the Methods in Biotechnology series. They begin with the theoretical and com- mercial background to the method or group of methods, provide a list of the reagents and equipment required for the procedure, then give a detailed step- by-step description of how to carry out the protocol. Each chapter concludes with a set of Notes, whose aim is to save the time of the user by indicating which problems are likely to arise and how best to deal with them.

The contributions begin with descriptions of methods for the production and isolation of microbial polysaccharides: the three polysaccharides selected--xanthan gum, microbial alginate, and schizophyllan---are of known commercial significance, and the methods described may be applied to the production of polysaccharides from other types or strains of microbes. The next three chapters describe the use of isolated enzymes in the synthesis and modification of polysaccharides (other than by hydrolysis). The core of the text concerns the production of smaller carbohydrate molecules, beginning

vi Preface

with the unusual cyclic oligosaccharides, cyclodextrins, and the microbial gly- colipids, some of which have most unexpected structures with considerable commercial potential. There follow eight contributions on the production of oligosaccharides: this may seem excessive, but many different approaches are employed to produce a great diversity of materials, some inexpensive prod- ucts for the food and animal feed industries, others very specialized structures for use by the pharmaceutical industry. Dr. Kren's contribution (Chap. 14) gives an example of the sophisticated chemo-enzymatic syntheses that are currently being developed for the preparation of complex oligosaccharides.

Enzymes coupled with physical methods, primarily electrophoresis, con- stitute the major means of determining the structures of nucleic acids. Until recently, analogous technology has not been available for the determination of carbohydrate structures. The FACE® method, described by Dr. Kumar and his colleagues (Chap. 18), remedies this lack.

The final group of chapters describes methods for producing and modi- fying low molecular weight carbohydrates. Dr. Elling's development (Chap. 19) of sucrose synthase-based syntheses of nucleotide sugars provokes opti- mism that the raw materials costs of producing oligosaccharides using "Leloir" glycosyltransferases may be lowered significantly. The later chapters describe, in general, the synthesis of simpler and cheaper products: sugars, sugar alcohols, and sugar derivatives. Finally, there is description of the use of an enzyme in the development of flavors in wines and fruit juices, a subject that will be of interest to those concerned with attempting to accelerate the maturation of wines.

It is intended that Carbohydrate Biotechnology Protocols should be read- able and readily intelligible. As a consequence, it should be of interest and value to synthetic chemists, fermentation technologists, and applied enzymolo- gists seeking information on the application of techniques--some familiar, some novel and very advanced---to produce compounds that may seem out of the ordinary. Most of all, it is hoped that this book will contribute to the advance of carbohydrate science, which is perhaps the last great area of molecular biology to be explored.

Christopher Bucke

Contents

Preface ............................................................................................................. v List of Contributors .......................................................................................... ix

1 Introduction to Carbohydrate Biotechnology Christopher Bucke ............................................................................................. 1

2 Production and Isolation of Xanthan Gum Fdlix Garcie-Ochoa, Victoria E. Santos, and Josd A. Casas ........................ 7

3 Alginate from A z o t o b a c t e r v ine land i i Francesca Clementi, Mauro Moresi, and Eugenio Parente ........................ 23

4 Production of Schizophyllan Udo Rau ............................................................................................................. 43

5 Enzymatic Synthesis of Cellulose Shiro Kobayashi, Shin.ichiro Shoda, Michael J. Donnel ly ,

and Stephen P. Church .............................................................................. 57 6 Modification of Alginate Using Mannuronan C-5-Epimerases

Helga Er tesv~g and Gudmund Sk j~k -B rmk .................................................. 71 7 Viscosity Control of Guar Polysaccharide Solutions

by Treatment with Galactose Oxidase and Catalase Enzymes Michael J. Donnelly ........................................................................................ 79

8 The Production of Cyclodextrins Using CGTase from Bac i l lus m a c e r a n s

Jacob A. Rendleman, J r .................................................................................. 89 9 Production of Microbial Glycolipids

Siegrnund Lang .............................................................................................. 103 10 Partial Enzymatic Hydrolysis of Starch to Maltodextrins

on the Laboratory Scale Leon M. Msrchal ............................................................................................. 119

11 The Production of ~(l~2)-Terminated Glucooligosaccharides Marguerite Dols, Vincent Monchois, Megali Remaud.Simdon,

Rend-Marc Willemot, and Pierre F. Monsan .......................................... 129 12 Enzymatic Production of F r u c t o o l i g o s a c c h a r i d e s from Sucrose

Jong Won Yun and Seung Koo Song .......................................................... 141 13 Enzymatic Production of Inulooligosaccharides from Inulin

J o n g Won Yun and Dong Hyun K i m ............................................................ 153

v//

v i i i C o n t e n t s

14 One-Pot Enzymatic Synthesis of Sialyl T-Epitope V l a d i m i r KEen .................................................................................................. 165

15 Hydrolysis of Hemicelluloses Using Combinations of Xylanases and Feruloyl Esterases

Craig B. Faulds, Paul A. Kroon, Bego~a Bartolome, and Gary Williamson ................................................................................ 183

16 Enzymatic Depolymerization of Chitins and Chitosans Riccardo A. A. Muzzarelli, Vesna Stanic, and Viviana Ramos ................. 197

17 Synthesis of Homo- and Hetero-Oligosaccharides from Underivatized Sugars Using Glycosidases

Christopher Bucke, John Packwood, Sony Suwasono, and Robert A. Rastafl ............................................................................... 213

18 Use of Fluorophore-Assisted Carbohydrate Electrophoresis (FACE®) in the Elucidation of N-Linked Oligosaccharide Structures

Harish P. M. K u m a r , Pa t r i c i a A. Denny, and P a u l C. D e n n y ..................... 221

19 Application of Sucrose Synthase in the Synthesis of Nucleotide Sugars and Saccharides

Astrid Zervosen and Lothar EIIing .............................................................. 235

20 Production of Isomaltulose Using Immobilized Bacterial Cells P e t e r S. J. Cheetham and Christopher Bucke ........................................... 255

21 The Production of Mannitol by Fermentation Wim Soetaert, Petra T. Vanhooren, and Erick J. Vandamme ................... 261

22 The Production of 3-Keto-Derivatives of Disaccharides Eberhard Stoppok and Klaus Buchholz ..................................................... 2 7 7

23 Enzymatic Synthesis of ~-Butylglucoside in a Biphasic Butanol-Water System Using the ~-Transglucosidase from A s p e r g i l l u s n i g e r

Marie-Pierre Bousquet, Rend-Marc Willemot, Pierre F. Monsan, F r a n c o i s Paul , and Emmanuel Boures ................................................... 291

24 Enzymatic Glycosylation of Aglycones of Pharmacological Significance

Yukio Suzuki and Kei Uchida ....................................................................... 2 9 7

25 Enzymatic Synthesis of Glycosides in Aqueous-Organic Two-Phase Systems and Supersaturated Substrate Solutions

Jeffrey A. Khan, Anna Millqvist-Fureby, and Evgeny N. V u l f s o n ............ 313

26 Use of 13-Glucosidase in the Development of Flavor in Wines and Fruit Juices

Yannick Gueguen, Patrick Chemardin, Guilhem Janbon, Alain Arnaud, and Pierre Galzy ............................................................... 323

Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 333

Contributors

ALAIN ARNAUD ° Chaire de Microbiologie Industrielle et de Gknetique des Micro-organismes, Ecole Nationale SupGrieure Agronomique de Montpellier, Montpellier, France

BEGOIqA BARTOLOME • Biochemistry Department, Institute of Food Research, Norwich Research Park, Norwich, UK

EMMANUEL BOURES ° ULICE, Zac "Les Portes de Riom, "Riom, France M A R ~ E - P I E R R E B O U S Q U E T ° Centre de Bioing~nierie Gilbert Durand,

Dkpartement de Gknie Biochemique et Alimentaire, INSA, UMR CNRS, LA INRA, Complexe Scientifique de Rangueil, Toulouse, France

KLAUS BUCHHOLZ • Department of Carbohydrate Technology, Technical University of Braunschweig, Braunschweig, Germany

CHRISTOPHER BUCKE • School of Biosciences, University of Westminster, London, UK

Jose A. CASAS ° Departamento de Ingeniera Quimica, Facultad Ciencias Quimicas, Universidad Complutense, Madrid, Spain

PETER S. J. CHEETHAM ° Zylepsis Ltd, Ashford, Kent, UK PATRICK CHEMARDIN ° DGpartement de Microbiologie Industrielle

et de Gknetique des Micro-organismes, Ecole Nationale Supkrieure Agronomique de Montpellier, Montpellier, France

STEPHEN P. CHURCH ° Ilex Close, Sunning Common, Reading, UK FRANCESCA CLEMENTI ° Dipartimento di Biotecnologie Agrarie

ed Ambientali, Universit5 degli Studi di Ancona, Ancona, Italy PATRICIA A. DENNY ° Biotechnology Group, Hyland Division, Baxter

Healthcare Corporation, Duarte, CA PAUL C. DENNY ° Biotechnology Group, Hyland Division, Baxter

Healthcare Corporation, Duarte, CA MARGUERITE DOLS • Centre de Bioingknierie Gilbert Durand, Dkpartement

de Gknie Biochemique et Alimentaire, INSA, UMR CNRS, LA INRA, Complexe Scientifique de Rangueil, Toulouse, France

MICHAEL J. DONNELLY ° AKZO NOBEL UK, plc, Coventry, UK

ix

Contributors xi

VINCENT MONCHO1S • Centre de Bioing&nierie Gilbert Durand, DOpartement de Gbnie Biochemique et Alimentaire, INSA, UMR CNRS, LA INRA, Complexe Scientifique de Rangueil, Toulouse, France

PIERRE F. MONSAN • Centre de Bioingknierie Gilbert Durand, Dkpartement de G~nie Biochemique et Alimentaire, INSA, UMR CNRS, LA INRA, Complexe Scientifique de Rangueil, Toulouse, France

MAURO MORESI • Istituto di Tecnologie Agroalimentari, University of Tuscia- Viterbo, Viterbo, Italy

RICCARDO A. A. MUZZARELLI ° Faculty of Medicine, Universitdt degli Studi di Ancona, Ancona, Italy

JOHN PACKWOOD ° School of Biosciences, University of Westminster, London, UK

EUGENIO PARENTE ° Dipartimento di Biologia Difesa e Biotecnologie Agro Forestali, Universitd degli Studi Della Basilicata, Potenza, Italy

FRANtTOIS PAUL ° Centre de Bioing~nierie Gilbert Durand, Dkpartement de Gknie Biochemique et Alimentaire, INSA, UMR CNRS, LA INRA, Complexe Scientifique de Rangueil, Toulouse, France

VIVIANA RAMOS ° Faculty of Medicine, Universitd degli Studi di Ancona, Ancona, Italy

ROBERT A. RASTALL ° Department of Food Science and Technology, University of Reading, Whiteknights, Reading, UK

UDO RAU • Biotechnology Group, Department of Biochemistry and Biotechnology, Technical University Braunschweig, Braunschweig, Germany

MAGALI REMAUD-SIMISON ° Centre de Bioingdnierie Gilbert Durand, D~partement de Gknie Biochemique et Alimentaire, INSA, UMR CNRS, LA INRA, Complexe Scientifique de Rangueil, Toulouse, France

JACOB A. RENDLEMAN, JR. ° Biopolymer Research Unit, National Center for Agricultural Utilization Research, USDA Agricultural Research Service, Peoria, IL

VICTORIA E. SANTOS ° Departamento de Ingeniera Quimica, Facultad Ciencias Quimicas, Universidad Complutense, Madrid, Spain

SHIN-ICHIRO SHODA ° Department of Materials Chemistry, Graduate School of Engineering, Tohoku University, Aoba, Sendai, Japan

GUDMUND SKJAK-BR~EK • The Norwegian Polymer Laboratory, Institute of Biotechnology, Norwegian University for Science and Technology, Trondheim, Norway

xii Contributors

WIM SOETAERT " L a b o r a t o r y of Industrial Microbiology and Biocatalysis, University of Ghent, Ghent, Belgium

SEUNC Koo SON~ • Department of Chemical Engineering, Pusan National University, Pusan, Korea

VESNA STANIC • Faculty of Medicine, Universit3 degli Studi di Ancona, Ancona, Italy

EBERHARD STOPPOK • Zuckerinstitut, Braunschweig, Germany SONY SUWASONO • Department of Food Science and Technology, University

of Reading, Whiteknights, Reading, UK YUKIO SUZUKI • Division of Biochemistry, Research Institute for Bioresources,

Okayama University, Kurashiki, Japan KEI UCHIDA • Division of Biochemistry, Research Institute for Bioresources,

Okayama University, Kurashiki, Japan ERICK J. VANDAMME • Laboratory of Industrial Microbiology

and Biocatalysis, University of Ghent, Ghent, Belgium PETRA T. VANHOOREN • Laboratory of Industrial Microbiology

and Biocatalysis, University of Ghent, Ghent, Belgium EVGENY N . VULFSON • Department of Macromolecular Sciences, Institute

of Food Research, Earley Gate, Reading, UK RENI~-MARC WILLEMOT • Centre de Bioing&nierie Gilbert Durand,

D~partement de GOnie Biochemique et Alimentaire, INSA, UMR CNRS, LA INRA, Complexe Scientifique de Rangueil, Toulouse, France

GARY WILLIAMSON • Institute of Food Research, Norwich Laboratory, Norwich Research Park, Norwich, UK

JONG WON YUN • Department of Biotechnology, Taegu University, Kyungbuk, Korea

ASTRID ZERVOSEN • Institute of Enzyme Technology, Heinrich-Heine- University Diisseldorf Research Center Jiilich, Jiilich, Germany