Distribution and Biological Role. The Chemistry and Biology of Compounds Containing Amino Sugars PDF
Preview Distribution and Biological Role. The Chemistry and Biology of Compounds Containing Amino Sugars
THE AMINO SUGARS The Chemistry and Biology of Compounds Containing Amino Sugars EDITED BY ROGER W. JEANLOZ and ENDRE A. BALAZS Volume IA Chemistry of Amino Sugars Volume IB Glycosaminoglycans, Glycoproteins, and Glycosaminolipids Volume HA Distribution and Biological Role Volume IIB Metabolism and Interactions THE AMINO SUGARS The Chemistry and Biology of Compounds Containing Amino Sugars VOLUME IIA DISTRIBUTION AND BIOLOGICAL ROLE EDITED BY ENDRE A. BALAZS and ROGER W. JEANLOZ Institute of Biological and Harvard Medical School and Medical Sciences-Retina Foundation and Massachusetts General Hospital Harvard Medical School Boston, Massachusetts Boston, Massachusetts 1965 ACADEMIC PRESS New York and London COPYRIGHT © 1965, BY ACADEMIC PRESS INC. ALL RIGHTS RESERVED. NO PART OF THIS BOOK MAY BE REPRODUCED IN ANY FORM, BY PHOTOSTAT, MICROFILM, OR ANY OTHER MEANS, WITHOUT WRITTEN PERMISSION FROM THE PUBLISHERS. ACADEMIC PRESS INC. Ill Fifth Avenue, New York, New York 10003 United Kingdom Edition published by ACADEMIC PRESS INC. (LONDON) LTD. Berkeley Square House, London W. 1 LIBRARY OF CONGRESS CATALOG CARD NUMBER: 62-13092 PRINTED IN THE UNITED STATES OF AMERICA LIST OF CONTRIBUTORS Numbers in parentheses refer to the pages on which the authors' contributions begin. E. A. BALAZS (281, 401), Department of Connective Tissue Research, Insti- tute of Biological and Medical Sciences, Retina Foundation; Department of Ophthalmology, Harvard Medical School, Boston, Massachusetts NORMAN F. BOAS (95), Department of Research, The Norwalk Hospital, Nor walk, Connecticut ZACHARIAS DISCHE (115), Department of Ophthalmology, College of Physi- cians and Surgeons, Columbia University, New York, New York SEN-ITIROH HAKOMORI (353), Laboratory for Carbohydrate Research, Massa- chusetts General Hospital, Boston, Massachusetts; and Department of Biochemistry, Tohoku Pharmaceutical School, Sendai, Japan DAVID HAMERMAN (257), Department of Medicine, Albert Einstein College of Medicine, Yeshiva University, New York, New York HELEN MTJIR (311), Medical Unit, St. Mary1 s Hospital, London, England LARS ODIN (141, 205), Clinical Chemistry Laboratory, Central County Hospital of Halmstad, Halmstad, Sweden R. H. PEARCE (149), Department of Pathology, Faculty of Medicine, Uni- versity of British Columbia, Vancouver, British Columbia, Canada NILS R. RINGERTZ (209), Department of Cell Research, Karolinska Insti- tute, Stockholm, Sweden H. J. ROGERS (281), National Institute for Medical Research, The Ridgeway Mill Hill, London, England MAXWELL SCHUBERT (257), Department of Medicine, New York University, College of Medicine, New York, New York NATHAN SHARON (1), Department of Biophysics, The Weizmann Institute of Science, Rehovoth, Israel ROBERT G. SPIRO (47, 79), Department of Biological Chemistry, Harvard Medical School; Elliott P. Joslin Research Laboratory, Boston, Massachusetts LARS SUNDBLAD (229), Central Research Laboratory, Södersjukhuset, Stock- holm, Sweden V νί List of Contributors LARS SVENNERHOLM (381), Department of Medical Biochemistry, University of Göteriburg, Götenburg, Sweden BENGT SYLVÉN (195), The Cancer Research Division of Radiumhemmet, Karolinska Sjukhuset, Stockholm, Sweden J. A. SZIRMAI (219, 251), Research Laboratories, Department of Rheumatol- ogy, University Hospital, Leiden, The Netherlands IVAR WERNER (141, 205), Department of Internal Medicine, University Hospital, Uppsala, Sweden RICHARD J. WINZLER (337), Department of Biological Chemistry, University of Illinois, College of Medicine, Chicago, Illinois PREFACE The rapid increase of knowledge in the field of amino sugar-containing compounds has inspired this four-volume treatise. It was felt that a sum- mary of the present knowledge, with a comprehensive review of the litera- ture, prepared by scientists currently working actively in this field, would provide a starting point for the newcomer to the field and would also serve the expert in the broadening of his interest. The purpose of this treatise is to survey the chemistry, physical chem- istry, and biochemistry of all naturally occurring and synthetically prepared amino sugars and amino sugar-containing molecules and to present a critical and interpretative account of the biological and medical importance of these molecules. The broad scope of the work resulted in a progressive extension of the subject into diverse areas, including such fields as protein, carbohydrate, and lipid chemistry, immunochemistry, histochemistry, bacteriology, virology, and pathology. It is hoped that this very first attempt to present a comprehensive and integrated account of this excit- ingly expanding field of knowledge will serve as a valuable tool for research and teaching, extending, in its usefulness, well beyond the main subject matter. In the organization of this treatise, the two most important considera- tions were the synthetic framework for the collection of the related subjects and the systematic treatment of the particular areas. The synthetic frame- work was provided by the multidisciplinary approach to a very specific subject which encompasses a variety of compounds and cuts across the regular specialization pattern of chemists, biochemists, and biologists. The pivotal point of the subject matter is the amino sugar molecule, a cross- breed between amino acids and carbohydrates, which is the only common building block of such diverse macromolecules as glycoproteins, glycolipids, and glycosaminoglycans. The selection of amino sugars as a common denominator for the descrip- tion of a variety of molecular entities of a widely differing chemical and physical nature was made, indeed, to stimulate a synthetic approach to the biological importance of these compounds. It seemed to us, as it no doubt has to many others before, that amino sugars occupy a central position on the chemical and biological levels. The chemist may see the amino group on a variety of carbohydrate skeletons as a common chemical determi- nant—not only in small molecules, but also buried in the complex secondary vii viii Preface and tertiary structures of macromolecules. The biologist may think about the common metabolic events of these nitrogenous monosaccharides, in- volving such diverse macromolecules as proteins, polysaccharides, and lipids, and he may wonder about the functional aspects of the underlying structural and metabolic similarities. A synthesis at the level of the scien- tific disciplines was attempted by gathering the viewpoints of the chemist, physical chemist, biochemist, and biologist on amino sugars and on macro- molecules that contain amino sugars and focusing the interest on the chemical and physical structures and on the biological interactions of these compounds. The systematic treatment of this broad subject dictated a careful sub- division of the material into four volumes and 51 chapters. Volume IA (Chapters 1-5) is devoted to the chemistry of amino sugars, including oligosaccharides, nucleotide derivatives, and glycosides of amino sugars. Volume IB (Chapters 6-17) presents the chemical and physical structure of macromolecules that contain amino sugars. Amino sugar-containing polysaccharides (glycosaminoglycans), peptides (glycopeptides), proteins (glycoproteins), and lipids (glycosaminolipids), from both chemical and physicochemical viewpoints, and the methods for their isolation, separa- tion, determination, and histochemical localization are reviewed. Volume IIA (Chapters 18-37) deals with the distribution and the biological role of amino sugars and amino sugar-containing macromolecules in plants and animals. This systematic review includes all living systems, organized according to tissues and organs, and represents a pioneering effort on the part of the authors. Volume IIB (Chapters 38-51) presents the metabolism of amino sugars and amino sugar-containing macromolecules and their interactions with other molecules, viruses, and cells, as well as with radia- tion. Concern for a comprehensive and systematic presentation of the subject resulted in a need for a careful balance between the avoidance of overlap and the maintenance of the integrity of the individual chapters. Whenever a conflict arose from these two opposite interests, we preferred to be repetitious rather than risk omission of an important aspect or expres- sion of the personal viewpoint of an author. Completeness of the treatise has been of particular importance and con- cern and has resulted in special treatment of the references. First, authors were encouraged to be inclusive, rather than selective, in the preparation of the bibliography for their respective chapters. Second, to ensure an up-to-date bibliography, a special effort was made to include literature published after the preparation of the manuscripts. Whenever it was justified, this was achieved by the addition of an addendum at the end of a chapter or by the insertion of a list of recent publications in the page proofs at the end of a chapter. Third, the literature citations of each chapter were Preface ιχ verified by the editorial staff in an attempt to provide the reader with a useful bibliography. Fourth, the bibliographies of all chapters were com- bined and are presented in one reference list-author index at the end of each volume. This was done in the hope that the reader would have less difficulty in locating a needed reference and would have a better survey of the publications of various authors in this field. The forty-seven authors of this treatise did not have an easy task. In most cases, they could not take a previously published review as a starting point, and, consequently, these chapters represent a pioneering effort. The organizational integrity of the treatise demanded that a logical sequence of chapters be maintained in a complete coverage of the subject. Since the treatise was prepared during a period of very rapid expansion in the field, the fulfillment of this goal made the task of the authors even more difficult and placed upon them a considerable hardship. Frequent personal consul- tations between the editors and the contributors aided greatly in clarifying some of the problems. Without the high degree of cooperative spirit and patience on the part of the authors, however, the publication of this treatise would never have been realized. For this, we wish to express to the authors our sincere thanks. Boston, Massachusetts ENDUE A. BALAZS April, 1965 ROGER W. JEANLOZ ACKNOWLEDGMENTS The editors wish to thank Mrs. Barker Fred for her invaluable assistance in the editorial work of this treatise, which has included verification of the bibliography, the copy editing of the text and the subject index, and, last but not least, linguistic correc- tions. The editors are grateful to Miss Edith Klatskin for her assistance in the organiza- tion of the treatise and in the handling of the voluminous correspondence throughout the years. They are also indebted to the following members of the Department of Con- nective Tissue Research of the Retina Foundation, Institute of Biological and Medical Sciences, for their assistance in the preparation of the subject index of Volume IIA: Drs. Arthur F. Howe, Sven E. Österlin, Donald S. Scheufele, David A. Swann, Denis B. Sweeney, Michèle Testa, and Laszlo Z. J. Toth. The following authors wish to acknowledge financial aid and other assistance in the preparation of their chapters: E. A. Balazs (Chapter 37)—This work was supported by PHS research grant B-3370 from the National Institute of Neurological Diseases and Blindness, U.S. Public Health Service. Norman F. Boas (Chapter 21)—Part of the work reported here has been supported by grants from the National Institute of Arthritis and Metabolic Diseases, U.S. Public Health Service, and from The Helen Hay Whitney Foundation. David Hamerman (Chapter 31)—This chapter was written during the author's tenure of a Markle Scholarship in Medical Science. This work was supported by Graduate Training Grant 2A-5082 from the National Institute of Arthritis and Metabolic Diseases, U.S. Public Health Service. R. H. Pearce (Chapter 24)—The author's research in this field has been generously supported by the Medical Research Council of Canada, the Canadian Arthritis and Rheumatism Society, and Federal health grants while in his former post in the Department of Pathological Chemistry, Faculty of Medicine, University of Western Ontario, London, Canada, as well as by the Medical Research Council of Canada in his present post. Dr. Q. T. Smith of the University of Minnesota and Dr. J. C. Houck of the Children's Hospital of Washington generously made their data available prior to publication. The continued interest and encourage- ment of Dr. E. M. Watson and Dr. H. E. Taylor are much appreciated. Miss J. M. Mathieson has assisted greatly in the search of the literature. Maxwell Schubert (Chapter 31)—This work was supported by PHS research grants A-28(C) and A-1431(C2) from the National Institute of Arthritis and Metabolic Diseases, U.S. Public Health Service. Robert G. Spiro (Chapters 19 and 20)—These chapters were written during the author's tenure of an Established Investigatorship of the American Heart Association. xi A GUIDE TO THE NOMENCLATURE The nomenclature used in this treatise represents an attempt to intro- duce some uniformity into a field in which scientists of many different backgrounds and interests are actively engaged. For many years, the committees on carbohydrate nomenclature of the American Chemical Society and of the Chemical Society of Great Britain have worked to develop a system of terminology which could be accepted internationally. The terms commonly used by biochemists, such as glucosamine, iV-acetyl- glucosamine, galactosamine, iV-acetylgalactosamine, muramic acid, and the like, have been replaced by their systematic names. These changes bring many advantages to the chemists, who are now able to name deriva- tives of these compounds in accordance with the accepted rules of carbo- hydrate nomenclature, but, to the biochemists, biologists, and medical scientists, they appear as unnecessary and cumbersome terms (e.g., 2-acet- amido-2-deoxyglucose or 2-amino-3-0-(D-l-carboxyethyl)-2-deoxy-D-glu- cose). Consequently, the editors decided to compromise. They have used the trivial names glucosamine, galactosamine, muramic acid, and the like, in Volumes IIA and IIB, which deal with the biochemical and biological aspects of amino sugars and their compounds. In Volumes IA and IB, however, which deal with the chemistry of these compounds, both the trivial and the systematic names are used. The term neuraminic acid is used for 5-&mmo-3,5-dideoxy-O-glycero-O-galacto-nomi\omc acid, and the term sialic acid is used as a group name for acylated neuraminic acids.* The problem was more complex in the case of substances of large molec- ular weight. The detailed chemical structure of many of these substances is still unknown. Frequently, the same terms have been used with many different meanings. Moreover, the committees on nomenclature have not made any formal recommendations for the naming of amino sugar-con- taining polymers. The prefix "muco," which originally was meant to indicate a viscous substance prepared from mucous membranes or glandular secretions, has been used over the years for a variety of substances having protein, carbo- hydrate, or lipid characteristics. The indiscriminate usage of such names as mucopolysaccharide, mucoprotein, mucolipid, mucosubstance, mucoid, and the like, has given different meanings to this prefix, thus adding to the * Blix, G., Gottschalk, A., and Klenk, E. 1957. Nature 179: 1088. xiii
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