Carbohydrate Research Vol. 375, 2013

Contents

REVIEW

Recent developments of ionic liquids in oligosaccharide synthesis: the sweet side of ionic liquids pp 35–46

M. Carmen Galan*, Rachel A. Jones, Anh-Tuan Tran

OLG

PO

IL/CH2Cl2r.t.

ROH

Recycling

IL

OORBnO

Product

N N+

-X

Ionic Liquids (IL)

Solvents and Promoters in Oligosaccharide Synthesis

Ionic Liquid Supported Oligosaccharide Synthesis

Carbohydrate Elongation

[m/z]LC-MS

Reaction MonitoringProductRELEASE

CLEAVABLE LINKER

CLEAVABLE LINKER

I-Tag

N N

+

N N

+

FULL PAPERS

Synthesis

A practical access to glucose- and allose-based (5+5) 3-spiropseudonucleosides from a common intermediate pp 5–15

M�aris Turks*, Vitalijs Rodins, Evija Rolava, P�avels Ostrovskis, Sergey Belyakov

Synthesis of all four stereoisomers of 5-formyl-4-hydroxymethyl-1,3-oxazolidin-2-ones from DD-glucosamine pp 47–54

Teiichi Murakami*

OHO

HO OH

NH

OH

O NH

O

PhO

O

OH

O NH

O

OHHOO

N-Phenoxycarbonyl-D-glucosamine

5-Formyl-4-hydroxymethyl-oxazolidinone

4,5-Bis(hydroxymethyl)-oxazolidinone

iii

Contents lists available at SciVerse ScienceDirect

Carbohydrate Research

journal homepage: www.elsevier .com/locate /carres

N-linked glycolipids by Staudinger coupling of glycosylated alkyl diazides with fatty acids pp 55–62

Salih Mahdi Salman, Thorsten Heidelberg*, Hairul Anuar Bin Tajuddin

One-pot synthesis of O-glycosyl triazoles by O-glycosylation–click reaction pp 79–89

Wadchara Mangsang, Uthaiwan Sirion, Rungnapha Saeeng*

Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy pp 118–135

Ying-Hsin Wang, Hsien-Wei Yeh, Hsiao-Wen Wang, Chia-Chun Yu, Jih-Hwa Guh, Der-Zen Liu, Pi-Hui Liang*

O

OH

OHO

OO

R2

R1

R1 and R2 = H, monosaccharide, or disaccharide

O

O

OOAc

OLevOBnO

OBn

ONPAc

O

O

OH

Hydrazine

Zn

glycosylation

glycosylation

deprotection

Biochemistry and Enzymes

Kinetic analysis of inhibition of glucoamylase and active site mutants via chemoselective oxime immobilizationof acarbose on SPR chip surfaces

pp 21–28

Jørgen Sauer, Maher Abou Hachem, Birte Svensson, Knud J. Jensen, Mikkel B. Thygesen*

iv Contents / Carbohydrate Research 375 (2013) iii–viii

Parallel quantification of lectin–glycan interaction using ultrafiltration pp 112–117

Yoichi Takeda*, Akira Seko, Masafumi Sakono, Masakazu Hachisu, Akihiko Koizumi, Kohki Fujikawa, Yukishige Ito*

Furfural degradation in a dilute acidic and saline solution in the presence of glucose pp 145–152

B. Danon*, L. van der Aa, W. de Jong

Characterization, Naturalproducts

Comparative analysis of flagellin glycans among pathovars of phytopathogenic Pseudomonas syringae pp 100–104

Kazuhiro Chiku, Masanobu Yamamoto, Mayumi Ohnishi-Kameyama, Tadashi Ishii, Mitsuru Yoshida, Fumiko Taguchi,Yuki Ichinose, Hiroshi Ono*

OH

O

O

O

MeO

NHAc

HO

HO

O

HO

HO

HN N

HO

OH

OH

O

O

OO

OMe

NH

HO

HO

OH

HO

HO

HN N

OOH

O

O

O

OO

OMe

NH

HO

HO

OH

HO

HO

OOH

OH

OHO

HO

HN N

Polysaccharides from the edible mushroom Calocybe gambosa: structure and chain conformation of a(1fi4),(1fi6)-linked glucan

pp 153–157

Ana Villares*

Contents / Carbohydrate Research 375 (2013) iii–viii v

Polysaccharides

Evaluation of carbohydrates and lignocellulosic biomass from different wood species as raw material for the synthesisof 5-bromomethyfurfural

pp 63–67

Aleksei Bredihhin, Uno Mäeorg, Lauri Vares*

Microwave-assisted rapid conversion of carbohydrates into 5-hydroxymethylfurfural by ScCl3 in ionic liquids pp 68–72

Xuanmu Zhou, Zehui Zhang*, Bing Liu, Zheng Xu, Kejian Deng*

OO

OH

ScCl3, [Bmim]Cl

HMF

OOH

OH

HOH2C

Sucrose

HOO

HO OH

HOOHO

Microwave irradiation

Yield in 73.4% for 2.5 min

High molecular weight plant heteropolysaccharides stimulate fibroblasts but inhibit keratinocytes pp 90–99

Munira Shahbuddin, Dahlia Shahbuddin, Anthony J. Bullock, Halijah Ibrahim, Stephen Rimmer, Sheila MacNeil*

Glucomannan

Ker

atin

ocyt

esFi

brob

last

s

Con A FITC stained mannose receptors and lectins on cell surface.

Live/Dead staining showing the effect of KGM. (Scale 200ηm)

Amorphophalluskonjac

The structure of the O-specific polysaccharide from marine bacterium Litorimonas taeanensisG5T containing 2-acetamido-4-((3S,5S)-3,5-dihydroxyhexanamido)-2,4-dideoxy-DD-quinovoseand2-acetamido-2,6-dideoxy-LL-xylo-hexos-4-ulose

pp 105–111

Maxim S. Kokoulin*, Anatoliy I. Kalinovsky, Nadezhda A. Komandrova,Victoria E. Tovarchi, Svetlana V. Tomshich, Ol’ga I. Nedashkovskaya, Victor E. Vaskovsky

vi Contents / Carbohydrate Research 375 (2013) iii–viii

Chemical shift assignment of the complicated monomers comprising cellulose acetate by two-dimensional NMRspectroscopy

pp 136–144

Hiroyuki Kono*

123

4 56

ppm

3.43.63.84.04.24.44.64.85.05.25.4 ppm

3.4

3.6

3.8

4.0

4.2

4.4

4.6

4.8

5.0

5.2

5.4

NOTES

Biochemistry and Enzymes

TMG-chitotriomycin as a probe for the prediction of substrate specificity of b-N-acetylhexosaminidases pp 29–34

Hiroto Shiota, Hiroshi Kanzaki, Tadashi Hatanaka, Teruhiko Nitoda*

Inhibitor 1(TMG-chitotriomycin)

1-sensitive 1-insensitive

β-N-acetylhexosaminidases (HexNAcases)

Enzymes involved in

chitin degradationEnzymes involved in

glycoconjugate processing

Characterization, Naturalproducts

A new cytotoxic triterpene saponin from Lysimachia nummularia L. pp 16–20

Irma Podolak*, Paulina Koczurkiewicz, Marta Michalik, Agnieszka Galanty, Paweł Zajdel, Zbigniew Janeczko

Polysaccharides

Structure of the O-polysaccharide of Providencia alcalifaciens O35 containing an N-[(S)-1-carboxyethyl]-LL-alanine(alanopine) derivative of 4-amino-4,6-dideoxyglucose

pp 73–78

Olga G. Ovchinnikova*, Olga A. Valueva, Nina A. Kocharova, Nikolay P. Arbatsky,Agnieszka Maszewska, Agnieszka Zablotni, Alexander S. Shashkov, Antoni Rozalski,Yuriy A. Knirel

Contents / Carbohydrate Research 375 (2013) iii–viii vii

Physical, X-Ray, Chromatography

Comparative decomposition kinetics of neutral monosaccharides by microwave and induction heating treatments pp 1–4

Shuntaro Tsubaki*, Kiriyo Oono, Ayumu Onda, Kazumichi Yanagisawa, Jun-ichi Azuma

*Corresponding authorSupplementary data available via SciVerse ScienceDirect

COVER

Multi-functionalisation of cyclodextrins (CD) has entered a new era thanks to the regioselective chemistry developed by M. Sollogoub’s group.As illustrated on the cover, many applications can now be reached using CDs with various functions on specific positions. An example offunctionalisation of CDs is given in the first issue of this journal. Image realised by Mickaël Ménand.

Available online at www.sciencedirect.com

Abstracted/Indexed in: Chem. Abstr.: Curr. Contents: Phys., Chem. & Earth Sci. Life Sci. Current Awareness in Bio. Sci. (CABS).Science Citation Index. Full texts are incorporated in CJELSEVIER, a file in the Chemical Journals Online database whichis availabe on STN� International. Also covered in the abstract and citation database SciVerse Scopus�. Full text available onSciVerse ScienceDirect�

ISSN 0008-6215

viii Contents / Carbohydrate Research 375 (2013) iii–viii