Advances in Carbohydrate Chemistry and Biochemistry Volume 29 This Page Intentionally Left Blank Advances in Carbohydrate Chemistry Biochemistry Editors R. STUART TIPSON DEREK HORTON Board of Advisors L. ANDERSON D. FRENCH W. W. PIGMAN ROY L. WHISTLER W. J. WHELAN Board of Advisors for the British Commonwealth A. B. FOSTER SIR EDMUNDHIRST J. K. N. JONES MAURICESTACEY Volume 29 ACADEMIC PRESS New York and London A Subsidiary of Harcourt Brace Jovanovich, Publishers 1974 COPYRIGHT 8 1974, 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 A N Y INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WRITING FROM THE PUBLISHER. ACADEMIC PRESS, INC. 111 Fifth Avenue, New York. New York 10003 United Kingdom Edition published by ACADEMIC PRESS, INC. (LONDON) LTD. 24/28 Oval Road, London NWI LIBRARY OF CONGRESS CATALOG CARD NUMBER:45-11351 PRINTED IN THE UNITED STATES OF AMERICA CONTENTS LISTOF CONTRIBUTORS................................................ PREFACE............................................................ ix X Bernard Randall Baker ( 1915-1971 ) LEONGOODMAN Text ............................................................... Appendix ........................................................... 1 10 Solutions to the Hidden-Resonance Problem in Proton Nuclear Magnetic Resonance Spectroscopy LAURANCE D. HALL . I Introduction ................................................... I1. Chemical Methods .............................................. I11. Physical Methods ............................................... IV. Conclusions .................................................... 11 13 25 39 Mass Spectrometry in Structural Analysis of Natural Carbohydrates JORGENLONNCREN AND SICFRID SVENSSON I . Introduction ................................................... I1. General Remarks ............................................... I11. Monosaccharide Glycosides ...................................... IV. Monosaccharide Alditols ......................................... V. Miscellaneous Monosaccharide Derivatives ......................... VI . Oligosaccharides ............................................... VII. Addendum .................................................... 42 42 43 51 71 84 106 The Electrochemistry of Carbohydrates and Their Derivatives MICHALFEDORO~KO I . Introduction ................................................... 107 I1. Electrosynthesis of Carbohydrates and Their Derivatives .............. 108 I11. Polarography of Carbohydrates and Their Derivatives ................ 126 Synthesis and Utilization of Formose Sugars TAWSHI MIZUNOAND ALVIN H . W ~ r s s I . History of Research on Formose .................................. I1. The Formose Reaction .......................................... V 173 180 vi CONTENTS I11. Sugar Composition of Formose ................................... IV. Biological Efficacy of Forniose ................................... V. Large-scale Production of Carbohydrate ............................ VI. Conclusion .................................................... 205 216 221 227 P-Eliminative Degradation of Carbohydrates Containing Uronic Acid Residues JOSEPH KISS . . I Introduction ..............................................