Carbohydrate Biotechnology Protocols

418 Pages·1999·6.05 MB·English

by  Christopher Bucke

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METHODS IN BIOTECHNOLOGY™
Carbohydrate Biotechnology Protocols
Edited by
Christopher Bucke
School of Biosciences,
University of Westminster, London, UK

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© 1999 Humana Press Inc.
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Totowa, New Jersey 07512
All rights reserved. No part of this book may be reproduced, stored in a retrieval system, or
transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming,
recording, or otherwise without written permission from the Publisher. Methods in
Biotechnology™ is a trademark of The Humana Press Inc.
All authored papers, comments, opinions, conclusions, or recommendations are those of the
author(s), and do not necessarily reflect the views of the publisher.
This publication is printed on acid-free paper.
ANSI Z39.48-1984 (American Standards Institute)
Permanence of Paper for Printed Library Materials.
Cover illustration: Scheme 1 from Chapter 14, “One-Pot Enzymatic Synthesis of Sialyl T-
Epitope” by Vladimir Kren *.
Cover design by Patricia F. Cleary.
For additional copies, pricing for bulk purchases, and/or information about other Humana titles,
contact Humana at the above address or at any of the following numbers: Tel.: [phone];
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Printed in the United States of America. 10 9 8 7 6 5 4 3 2 1
Library of Congress Cataloging in Publication Data
Main entry under title:
Methods in biotechnology™.
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. 1. Bucke, C.
II. Series.
TP248.65.P64C37 1999
660.6' 3—dc21 98-48663
CIP
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METHODS IN BIOTECHNOLOGY™
John M. Walker, S E
ERIES DITOR
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

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METHODS IN BIOTECHNOLOGY™
John M. Walker, S E
ERIES DITOR
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

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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 appreciated more fully. Progress in providing hard facts
to establish the commercial value of polysaccharides 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 containing many different monomers. Modern 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 commercial 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

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with the unusual cyclic oligosaccharides, cyclodextrins, and the microbial glycolipids, 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
products 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, constitute 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 modifying low molecular
weight carbohydrates. Dr. Ellling's development (Chap. 19) of sucrose synthase-based syntheses
of nucleotide sugars provokes optimism 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 readable and readily
intelligible. As a consequence, it should be of interest and value to synthetic chemists,
fermentation technologists, and applied enzymologists 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

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Contents
Preface v
List of Contributors ix
1 1
Introduction to Carbohydrate Biotechnology
Christopher Bucke
2 7
Production and Isolation of Xanthan Gum
Félix García-Ochoa, Victoria E. Santos, and José A. Casas
3 23
Alginate from Azotobacter vinelandii
Francesca Clementi, Mauro Moresi, and Eugenio Parente
4 43
Production of Schizophyllan
Udo Rau
5 57
Enzymatic Synthesis of Cellulose
Shiro Kobayashi, Shin-ichiro Shoda, Michael J. Donnelly,
and Stephen P. Church
6 71
Modification of Alginate Using Mannuronan C-5-
Epimerases
Helga Ertesvåg and Gudmund Skjåk-Bræk
7 79
Viscosity Control of Guar Polysaccharide Solutions by
Treatment with Galactose Oxidase and Catalase Enzymes
Michael J. Donnelly
8 89
The Production of Cyclodextrins Using CGTase from
Bacillus macerans
Jacob A. Rendleman, Jr.
9 103
Production of Microbial Glycolipids
Siegmund Lang
10 119
Partial Enzymatic Hydrolysis of Starch to Maltodextrins on
the Laboratory Scale
LeonM.Marchal
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Leon M. Marchal
11 129
The Production of α(1→2)-Terminated
Glucooligosaccharides
Marguerite Dols, Vincent Monchois, Magali Remaud-
Siméon, René-Marc Willemot, and Pierre F. Monsan
12 141
Enzymatic Production of Fructooligosaccharides from
Sucrose
JongWon Yun and Seung Koo Song
13 153
Enzymatic Production of Inulooligosaccharides from Inulin
Jong Won Yun and Dong Hyun Kim

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14 165
One-Pot Enzymatic Synthesis of Sialyl T-Epitope
Vladimír Kren *
15 183
Hydrolysis of Hemicelluloses Using Combinations of Xylanases and
Feruloyl Esterases
Craig B. Faulds, Paul A. Kroon, Begoña Bartolomé, and Gary Williamson
16 197
Enzymatic Depolymerization of Chitins and Chitosans
Riccardo A. A. Muzzarelli, Vesna Stanic, and Viviana Ramos
17 213
Synthesis of Homo- and Hetero-Oligosaccharides from Underivatized
Sugars Using Glycosidases
Christopher Bucke, John Packwood, Sony Suwasono, and Robert A.
Rastall
18 221
Use of Fluorophore-Assisted Carbohydrate Electrophoresis (FACE®) in the
Elucidation of N-Linked Oligosaccharide Structures
Harish P. M. Kumar, Patricia A. Denny, and Paul C. Denny
19 235
Application of Sucrose Synthase in the Synthesis of Nucleotide Sugars and
Saccharides
Astrid Zervosen and Lothar Elling
20 255
Production of Isomaltulose Using Immobilized Bacterial Cells
Peter S. J. Cheetham and Christopher Bucke
21 261
The Production of Mannitol by Fermentation
Wim Soetaert, Petra T. Vanhooren, and Erick J. Vandamme
22 277
The Production of 3-Keto-Derivatives of Disaccharides
Eberhard Stoppok and Klaus Buchholz
23 291
Enzymatic Synthesis of α-Butylglucoside in a Biphasic Butanol—Water
System Using the α-Transglucosidase from Aspergillus niger
Marie-Pierre Bousquet, René-Marc Willemot, Pierre F. Monsan, François
Paul, and Emmanuel Boures
24 297
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