Biology of the Sialic Acids

386 Pages·1995·8.75 MB·English

by  Abraham Rosenberg (auth.)

Biology of the
Sialic Acids
Biology of the
Sialic Acids
Edited by
Abraham Rosenberg
University of California, Los Angeles
Los Angeles, California
SPRINGER SCIENCE+BUSINESS MEDIA, LLC
Llb~a~y of Cong~ess Cataloging-In-Publication Data
Biology of the sialic acids I edited by Abraham Rosenberg.
p. em.
Includes bibliographical ·references and Index.
ISBN 978-1-4757-9506-6 ISBN 978-1-4757-9504-2 (eBook)
DOI 10.1007/978-1-4757-9504-2
1. Sialic acids--Physiological effect. I. Rosenberg, Abraham,
1924-
0P801.S47B566 1995
574.19'24--dc20 95-19224
CIP
ISBN 978-1-4757-9506-6
© 1995 Springer Science+Business Media New York
Originally published by Plenum Press, New York in 1995
Softcover reprint of the hardcover 1st edition 1995
10 9 8 7 6 54 3 2 1
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
Contributors
Manju Basu Department of Chemistry and Biochemistry, University of
Notre Dame, Notre Dame, Indiana 46556
Shih Sankar Basu Department of Chemistry and Biochemistry, University
of Notre Dame, Notre Dame, Indiana 46556
Subhash Basu Department of Chemistry and Biochemistry, University of
Notre Dame, Notre Dame, Indiana 46556
Veer P. Bhavanandan Department of Biochemistry and Molecular Biology,
The Milton S. Hershey Medical Center, Pennsylvania State University,
Hershey, Pennsylvania 17033
Kiyoshi Furukawa Department of Biochemistry, Institute of Medical Sci-
ence, Univeristy of Tokyo, Tokyo 108, Japan; present address: Department
of Biosignal Research, Tokyo Metropolitan Institute of Gerontology, Tokyo
173, Japan
Sen-itiroh Hakomori The Biomembrane Institute, and Departments of Pa-
thobiology and Microbiology, University of Washington, Seattle, Washing
ton 98195
Jiirgen Hausmann Virology Institute, University of Marburg, D-35037
Marburg, Germany
Georg Herrler Virology Institute, University of Marburg, D-35037 Mar-
burg, Germany
Masao lwamori Department of Biochemistry, Faculty of Medicine, The
University of Tokyo, Tokyo 113, Japan
v
vi Contributors
Sorge Kelm Biochemistry Institute, University of Kiel, D-24098 Kiel, Ger-
many
Hans-Dieter Klenk Virology Institute, University of Marburg, D-35037
Marburg, Germany
Yoshitaka Nagai Mitsubishi Kasei Institute of Life Sciences; Machida City,
Tokyo, and the Glycobiology Research Group, Frontier Research Program,
The Institute of Physical and Chemical Research (RIKEN), Wako City,
Saitama, Japan
GerdReuter Biochemistry Institute, University of Kiel, D-24098 Kiel, Ger-
many
Peter Roggentin Biochemistry Institute, University of Kiel, D-24098 Kiel,
Germany
Abraham Rosenberg Neuropsychiatric Institute and Brain Research In-
stitute, University of California, Los Angeles, Los Angeles, California
90024-1759
Megumi Saito Department of Biochemistry and Molecular Biophysics,
Medical College of Virginia, Virginia Commonwealth University, Rich
mond, Virginia 23298
Roland Schauer Biochemistry Institute, University of Kiel, D-24098 Kiel,
Germany
Lee Shaw Biochemistry Institute, University of Kiel, D-24098 Kiel, Ger-
many
Kunihiko Suzuki Brain and Development Research Center, Departments of
Neurology and Psychiatry, University of North Carolina School of Medi
cine, Chapel Hill, North Carolina 27599
Frederic A. Troy II Department of Biological Chemistry, University of
California, School of Medicine, Davis, California 95616
Robert K. Yu Department of Biochemistry and Molecular Biophysics,
Medical College of Virginia, Virginia Commonwealth University, Rich
mond, Virginia 23298
Preface
Breakthroughs worldwide have placed the cellular and molecular biology of the
sialic acids in the forefront of current scientific inquiry. The accumulating wealth
of new information in this field of study is presented in this volume for use by
both students and experts. The contributing authors are highly ranked among
those presently building up the store of knowledge gained from this very lively
international research effort. It is with wonderment that I have come to realize
that their gifts of knowledge are made at the time of my seventieth birthday. This
book is dedicated with great affection to my wife, Estelle, to my children, Ruth
Ann and Jonathan, to their mates, Stephen and Anne-Marie, and to grandson
Turner.
Abraham Rosenberg
vii
Contents
Chapter 1
The Beginnings of Sialic Acid
Abraham Rosenberg
I. Introduction ........................................... .
2. Discovery of Sialic Acid ................................ .
3. Scaling the Sialic Acid Structure . . . . . . . . . . . . . . . . . . . . . . . . . . . 2
4. How Sialobiology Began . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
Chapter 2
Biochemistry and Role of Sialic Acids
Roland Schauer, Sorge Keirn, Gerd Reuter, Peter Roggentin,
and Lee Shaw
I. Introduction 7
2. Occurrence of Sialic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12
3. Sialic Acid Analysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 16
4. Enzymatic Modifications of Sialic Acids . . . . . . . . . . . . . . . . . . . . 21
4.1. a-Acylation of Sialic Acids . . . . . . . . . . . . . . . . . . . . . . . . . 21
4.2. De-a-Acetylation of Sialic Acids . . . . . . . . . . . . . . . . . . . . . 22
4.3. a-Methylation of Sialic Acids . . . . . . . . . . . . . . . . . . . . . . . . 23
4.4. N-Acetyl-Hydroxylation of Sialic Acids . . . . . . . . . . . . . . . . 24
5. Relationship and Evolutionary Distribution of
Microbial Sialidases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31
6. Sialic Acid-Dependent Receptors and Their Ligands . . . . . . . . . . . 36
6.1. Occurrence . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36
6.2. Selectins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
ix
x Contents
6.3. CD22 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43
6.4. Sialoadhesin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44
6.5. Other Mammalian Sialic Acid-Dependent Receptors . . . . . . 45
6.6. Ligands for Sialic Acid-Dependent Receptors . . . . . . . . . . . 45
6. 7. Modifications of Sialic Acids . . . . . . . . . . . . . . . . . . . . . . . . 48
6.8. Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
Chapter 3
Biological Specificity of Sialyltransferases
Subhash Basu, Manju Basu, and Shib Sankar Basu
1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69
2. Sialyltransferases Catalyzing Sialooligosaccharides and
Sialoglycoprotein Biosynthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71
3. Sialyltransferases Catalyzing Sialoglycolipid Biosynthesis . . . . . 73
3.1. Ganglio- and Globo-Family Glycolipids . . . . . . . . . . . . . . . 73
3.2. Lacto-Family Glycolipids . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
4. Sialyltransferases Catalyzing Mucin Biosynthesis . . . . . . . . . . . . 79
5. Posttranslational Distribution of Sialyltransferases in
Golgi Membranes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 79
6. Cloning of a2-3 Sialyltransferases . . . . . . . . . . . . . . . . . . . . . . . . . 80
7. Cloning of a2-6 Sialyltransferases . . . . . . . . . . . . . . . . . . . . . . . . . 82
8. Cloning of a2-8 Sialyltransferases . . . . . . . . . . . . . . . . . . . . . . . . . 83
9. Modulation of Sialyltransferases in Developing Tissues . . . . . . . 84
10. Regulation of Sialyltransferases in Cancer Cells . . . . . . . . . . . . . 84
11. Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86
Chapter 4
Sialobiology and the Polysialic Acid Glycotope: Occurrence,
Structure, Function, Synthesis, and Glycopathology
Frederic A. Troy II
1. Introduction and Perspective . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95
2. Natural Occurrence and Structure of Polysialic Acid-Containing
Glycoconjugates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97
2.1. Prokaryotes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97
2.2. Eukaryotes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 99
Contents xi
3. Function of Polysialylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 107
3 .1. Bacterial Pathogenicity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 108
3.2. Teleost Fish Oogenesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 108
3.3. Sea Urchin Embryogenesis . . . . . . . . . . . . . . . . . . . . . . . . . . 109
3.4. Neurobiology . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 110
3. 5. Tumor Metastasis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 112
4. Biosynthesis of the Polysialic Acid Glycotopes . . . . . . . . . . . . . . . 114
4.1. The CMP-Sia:a2,8-polysialyltransferase Complex in
Neuroinvasive Escherichia coli K1 . . . . . . . . . . . . . . . . . . . . 114
4.2. Rainbow Trout Egg Polysialoglycoproteins . . . . . . . . . . . . . 122
4.3. Sea Urchin Embryo . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127
4.4. Fetal Rat and Embryonic Chick Brains . . . . . . . . . . . . . . . . 128
5. Identification of Polysialic Acid and Oligo-Poly
KDN Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 129
5.1. General Strategy: Immunochemical Detection Using
Anti-Polysialic Acid and Anti-KDN Antibodies . . . . . . . . . 129
5.2. Endo-N-acylneuraminidase (Endo-N): Specific Molecular
Probe to Detect and Structurally Modify a2,8-Linked
Polysialic Acid Chains . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 130
5.3. Discovery and Use of a New Type of Sialidase,
"KDNase," to Confirm the Identification of KDN-
Containing Glycoconjugates . . . . . . . . . . . . . . . . . . . . . . . . . 131
5.4. Use of the E. coli K1 Poly-a2,8-sialyltransferase to
Identify Preexisting a2,8-Linked Oligo-Polysialic
Acid Chains . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 131
6. Concluding Remarks and Future Directions . . . . . . . . . . . . . . . . . . 132
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 133
Chapter 5
Biochemistry and Oncology of Sialoglycoproteins
Veer P. Bhavanandan and Kiyoshi Furukawa
1. General Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 145
2. Classification and Nomenclature . . . . . . . . . . . . . . . . . . . . . . . . . . . 146
3. Oligosaccharide Structures of Sialoglycoproteins . . . . . . . . . . . . . . 146
3.1. Asn-Linked Saccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 147
3.2. Ser/Thr-Linked Saccharides . . . . . . . . . . . . . . . . . . . . . . . . . . 151
3.3. Polylactosaminoglycans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 154
4. Protein Core of 0-Linked Sialoglycoproteins . . . . . . . . . . . . . . . . . 155
5. Biosynthesis of Sialoglycoproteins . . . . . . . . . . . . . . . . . . . . . . . . . . 161
5. 1. General Concepts . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 161