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Advances in Carbohydrate Chemistry and Biochemistry, Volume 51 Advances in Carbohydrate Chemistry and Biochemistry Volume 51 This Page Intentionally Left Blank Advances in Carbohydrate Chemistry and Biochemistry Editor DEREK HORTON The American University Washington, DC Board of Advisors LAURENSANDERSON GUY G. S. DUTTON STEPHENJ. ANGYAL STEPHEN HANESSIAN HANS H. BAER BENGTLINDBERG CLINTONE. BALLOU HANSPAULSEN JOHN S. BRIMACOMBE NATHAN SHARON J. GRANT BUCHANAN J. F. G. VLIEGENTHART Roy L. WHISTLER Volume 51 ACADEMIC PRESS San Diego New York Boston London Sydney Tokyo Toronto This book is printed on acid-free paper. @ Copyright 0 1995 by ACADEMIC PRESS, INC. All Rights Reserved. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopy, recording, or any information storage and retrieval system, without permission in writing from the publisher. Academic Press, Inc. A Division of Harcourt Brace & Company 525 B Street, Suite 1900, San Diego, California 92101-4495 United Kingdom Edition published by Academic Press Limited 24-28 Oval Road, London NW 1 7DX International Standard Serial Number: 0065-23 18 International Standard Book Number: 0- 12-00725 1-3 PRINTED IN THE UNlTED STATES OF AMERICA 95 96 9798 99 00BB 9 8 7 6 5 4 321 CONTENTS PREFACE .................................................................. vii Horace S. Isbell, 1898-1992 HASSAN S. EL KHADEM I. The Scientific Achievements of Horace S. Isbell ........................ 1 Carbon-Proton Coupling Constants in the Conformational Analysis of Sugar Molecules IGOR TVAROSKAAND mANCOlS R. TARAVEL I. Introduction .......................................................... 15 11. General Theoretical Background 17 111. Experimental Techniques for Ob Coupling Constants. .. ............. 18 IV. Theory of Nuclear Spin-Spin Coupling Constants. ........................... 23 V. Conformational Dependence of Carbon-Proton ................................ 29 VI. Conclusion 57 57 Carbon-13 Nuclear Magnetic Relaxation and Motional Behavior of Carbohydrate Molecules in Solution PHOTIS DAIS 1. Introduction. .............................. .............. 63 11. Theory.. ..... .................................. ... 65 111. Dynamic Modeling .......... ............................. 74 .......................... .............................. 127 V vi CONTENTS Mechanisms in the Glucansucrase Synthesis of Polysaccharides and Oligosaccharides from Sucrose JOHN F . ROB= I . Historical Background and Structures of the Polysaccharides.................... 133 11 . Sources and Characteristics of the Enzymes ................................. 138 I11 . Mechanisms of Polysaccharide Synthesis ................................... 139 IV . Acceptor Reactions-Synthesis of Oligosaccharides and BranchingofDextrans .................................................. 151 V . Formulation and Kinetics of the Glucansucrase Reactions ...................... 163 References........................................................... 164 The Variable Surface Glycolipids of Mycobacteria: Structures. Synthesis of Epitopes. and Biological Properties GERALD0 . ASPINALL. DELPHI CHA'ITERIEE. AND PATRICK J . BRENNAN I . Introduction ...... ............................. 169 11 . Isolation and Fracti Structural Approaches ............................. .. ... 171 111. Structures of the Species- and Type-Specific Glycolipids of Mycobacteria....................................................... 175 IV . Synthesis and Antigenicity of Glycolipid-Based Neoglycoconjugates.................................................... 203 V. Other Biological Features of the Glycolipids of Mycobacteria ................... 229 References ........................................................... 236 Nonconventional Methods of Modification of Starch PIOTRTOMASIK AND MARKF . ZARANYIKA I. Introduction .......................................................... 243 n . Solvent Effects . ......................... 248 111 . 254 IV . Irradiation of Starch with Neutrons. X.Rays. High-Energy Electrons. and ?Rays ... 263 V . Visible and Ultraviolet Irradiation..................... 292 VI . ThermalEffects ................................... 296 VII . Ultrasonic Irradiation................................................... 302 VIII . Electrical Phenomena .............. ................................ 307 References .......................... 310 APPENDM ................................................................. 319 AUTHORINDEXFORVOLUME51.............................................. 321 SUSIEC~INDW(FORVOLUMES~.............................................. 341 PREFACE Structural sugar chemistry received its key foundations in work by German, British, and American investigators during the late 19th and the first half of the 20th century. These investigatorsemployed the classical tools of organic chemistry in conjunction with the physical technique of polarimetry and pioneering applica- tions of X-ray crystallography. However, many complex problems of tautomerism posed by sugars and their derivatives, along with questions concerning their con- formations and reactivities, resisted solution until the advent of more powerful analytical methods. It is noteworthy that development of the most significant of these techniques-NMR spectroscopy-as it rose to its prominent role as a structural tool in chemistry and biochemistry, owes much to the carbohydrate field and to the seminal work in the 1950s of R. U. Lemieux. Considered a mature technique in all areas of science, NMR spectroscopy has passed from being used for the simple recording and interpretation of chemical shiftsand spin couplings for small molecules to the domain of specialists perform- ing a multitude of procedures designed to extract detailed NMR parameters from biomolecules of ever-increasing complexity. In this volume of Advances, two chapters are devoted to current aspects of NMR spectroscopy. Tvaroska and Taravel (Bratislava and Grenoble) discuss carbon-proton coupling constants from both the experimental and theoretical points of view and address the significanceof these couplings in elucidating the conformational behavior of sugars and their derivatives. The extensive tabular information relating these couplings to dihedral angles in conformationally rigid molecules will constitute an important source of reference for other workers probing the three-dimensional structures of carbohy- drates in solution. A complementary article by Dais (Iraklion, Crete) addresses the theoretical principles underlying the phenomenon of carbon- 13 nuclear magnetic relaxation, encompassing spin-lattice (T,)and spin-spin (T2)relaxation times, the nuclear Overhauser enhancement, and their relation to the motional behavior of carbohy- drates in solution. With examples broadly selected from simple sugar derivatives, oligosaccharides, and polysaccharides, the author shows how qualitative treat- ments have provided useful interpretations of the gross mobility of molecules in solution, but demonstrates how a quantitative approach may be of greater ultimate value. Advances has regularly featured articles focusing on specific enzymes or en- zyme groups acting on carbohydrates. The article by Robyt (Ames, Iowa) in this volume is devoted to the glucansucraseenzymes and the mechanism whereby they utilize sucrose to transfer glucose to acceptors and elaborate polysaccharides of the dextran class, including the commercially important dextran from the B-512F strain of Leuconostoc mesenteroides. vii ... Vlll PREFACE Aspinall (York, Ontario) and Chatterjee and Brennan (Fort Collins, Colorado), in their article on the surface glycolipids of mycobacteria, focus on the chemistry and biology relating especially to an old medical problem, tuberculosis. This disease remains the leading cause of death from a single infectious agent. After years of decline in industrialized countries, TB is now showing a rapid increase that has some correlation with the incidence of HIV infection. The lipo-oligosaccharide antigens of these bacteria are of extraordinary complexity and variety posing, until recently, major problems of separation and structural characterization. This article brings together a comprehensive survey of isolation methodology and structural detail with a wealth of synthetic virtuosity that has been applied to the construction of oligosaccharide haptens of these antigens. Elaboration of such synthetic oligo- saccharide derivatives into neoglycoconjugateshas afforded a major tool for prob- ing antibody-antigen interactions and for developing immunlogicalprocedures in general. The final chapter by Tomasik and Zaranyika (Harare, Zimbabwe) deals with an aspect of carbohydrate technology that complements the article by Tomasik and co-workers in Volume 47 on the thermal decomposition of starch. The survey presented in this volume deals with the modifications taking place in starch when it is irradiated by various energy sources, ranging from ionizing radiation to ultra- sound, and by such treatments as freeze-thaw cycles and dehydration. Such treatments may impart little visible change to native starch granules, but may profoundly affect the behavior of the material in important technological and nutritional applications. The life and work of Horace S. Isbell, who ranked with Claude S. Hudson and Melville L. Wolfrom as one of the great American carbohydrate chemistry pio- neers, are presented here by El Khadem (Washington,DC). During his long career, Isbell made important fundamental discoveries in conformational analysis
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