Table Of ContentTHE 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 IIA Distribution and Biological Role
Volume MB Metabolism and Interactions
THE AMINO SUGARS
The Chemistry and Biology of Compounds
Containing Amino Sugars
VOLUME IIB
METABOLISM AND INTERACTIONS
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
1966
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LIST OF CONTRIBUTORS
Numbers in parentheses refer to the pages on which the authors' contributions begin.
ENDRE A. BALAZS (229, 361), Department of Connective Tissue Research,
Institute of Biological and Medical Sciences, Retina Foundation;
Department of Ophthalmology, Harvard Medical School, Boston,
Massachusetts
PETER BERNFELD (213, 251), Bio-Research Institute, Cambridge, Massa
chusetts
HARRY BOSTRÖM (45), Department of Metabolic Research, The Wenner-
Gren Institute, University of Stockholm, and the Department of
Medicine, Serafimerlasarettet, Karolinska Institutet, Stockholm,
Sweden
EUGENE A. DAVIDSON (1), Department of Biochemistry, Duke University
Medical Center, Durham, North Carolina
K. S. DODGSON (201), Department of Biochemistry, University of Wales,
Cardiff, Wales
HEINZ GIBIAN (181), Schering AG, Berlin, Germany
ALFRED GOTTSCHALK (337), Max-Planck-Institut für Virusforschung,
Tubingen, West Germany
BERNARD JACOBSON (361), Department of Connective Tissue Research,
Institute of Biological and Medical Sciences, Retina Foundation,
Boston, Massachusetts
MAX E. RAFELSON, JR. (171), Department of Biochemistry, Presbyterian-
St. Luke's Hospital, and the University of Illinois College of Medi
cine, Chicago, Illinois
LENNART RODEN (45), La Rabida-University of Chicago Institute, and
the Department of Biochemistry, The University of Chicago, Chi
cago, Illinois
MICHAEL SCHNEIR (171), Department of Biochemistry, Presbytenan-
St. Luke's Hospital, and the University of Illinois College of Medi
cine, Chicago, Illinois
VI List of Contributors
GEORG F. SPRINGER (267), Department of Immunochemistry Research,
Evanston Hospital Association and Department of Microbiology,
Northwestern University Medical School, Evanston, Illinois
LARS SUNDBLAD (229), Department of Clinical Chemistry, Södersjukhuset,
Stockholm, Sweden
J. A. SZIRMAI (129), Research Laboratories, Department of Rheuma
tology, University Hospital, Leiden, The Netherlands
PETER G. WALKER (155), The Institute of Orthopaedics, Royal National
Orthopaedic Hospital, Stanmore, Middlesex, England
VANNIE W. WILSON, JR. (171), Department of Biochemistry, Presbyter-
ian-St. Luke's Hospital, and the University of Illinois College of
Medicine, Chicago, Illinois
IKUO YAMASHINA (81), Faculty of Pharmaceutical Sciences, Kyoto Uni
versity, Sakyo-Ku, Kyoto, Japan
PREFACE
The rapid increase of knowledge in the field of amino sugar-contain
ing compounds has inspired this treatise. It was felt that a summary of
the present knowledge, with a comprehensive review of the literature,
prepared by scientists currently working 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 twofold: (1) to survey the chemistry,
physical chemistry, and biochemistry of all naturally occurring and
synthetically prepared amino sugars and amino sugar-containing mole
cules and (2) to present a critical and interpretative account of the
biological and medical importance of these molecules. The broad scope
of the work has 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 first attempt to present a comprehensive
and integrated account of this excitingly expanding field of knowledge
will serve as a valuable tool for research and teaching, extending, in its
usefulness, well beyond the main subject matter.
The organization of this treatise was dictated by the systematic
treatment of this broad subject. 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 physicochemical structure of amino sugar-
containing polysaccharides (glycosaminoglycans), peptides (glycopep-
tides), proteins (glycoproteins), and lipids (glycolipids), and the methods
for their isolation, determination, and histochemical localization. Volume
IIA (Chapters 18-37) deals with the distribution and biological role of
amino sugars and amino sugar-containing macromolecules in plants and
animals.
The present volume was prepared with two main purposes in mind.
One was to review the metabolism of the amino sugars and the amino
sugar moieties of macromolecules. Not only are the biosynthetic processes
presented in detail, but also the degradation of these macromolecules by
enzymes, oxidation-reduction systems, and radiation. Inasmuch as this
treatise is focused on amino sugars, the biosynthetic and degradation
processes which involve the protein, peptide, or lipid part of the macro
molecules are not reviewed.
vii
viii Preface
The second purpose of this volume is to review the interaction of
amino sugars, glycosaminoglycans, glycoproteins, and glycolipids with
other macromolecules, as well as with viruses, cells, and the whole
organism. This objective presented the editors with the difficult task of
carefully selecting the subjects to be included. Several amino sugar-
containing macromolecules are involved in biological processes and
pharmacological reactions of great importance, such as the blood-group
reactions of some glycoproteins and the prevention of blood coagulation
by heparin; a review of all the biological and pharmacological aspects
of these interactions would, however, have needed several additional
volumes and would have led to an undesirable dilution of the main
theme. The editors, therefore, decided to cover the pharmacological
aspects of the interaction of amino sugars and their compounds only
superficially and to refer the reader to recent reviews dealing with the
subject in detail.
The editors regret that the present volume, which represents the last
in the series of four comprising this treatise, is only the second to appear
in print. The delay of the publication of Volumes IA and IB has been
caused by the rapid growth of the field and the subsequent compelling
desire of the editors and authors to incorporate this never-ending expan
sion of knowledge in a systematic and comprehensive way.
In the Preface to Volume IIA, the editors recorded their appreciation
for the cooperation and patience of the contributors to this treatise. It
is appropriate to reiterate our thanks to the sixteen authors of the
fourteen chapters of Volume IIB who had not only the difficult chore of
reviewing a prolific field but often the pioneering task of canvassing and
compiling the literature according to new points of view.
ENDRE A. BALAZS
ROGER W. JEANLOZ
Boston, Massachusetts
January, 1966
NOMENCLATURE
The nomenclature used in this volume is identical to that used in
Volume IIA of this treatise. In order to avoid repetition, the reader is
referred, for details, to "A Guide to the Nomenclature" on page xiii of
Volume IIA of The Amino Sugars.
For immediate accessibility, some old terms and the few new ones are
listed below.
Chondroitin 4-sulfate — formerly called chondroitin sulfate A
Chondroitin 6-sulfate — formerly called chondroitin sulfate C
Dermatan sulfate — formerly called chondroitin sulfate B
Galactosaminoglycans — polysaccharides that contain galactosamine
Glucosaminoglycans — polysaccharides that contain glucosamine
Glycoproteins — proteins that contain sugars
Glycosaminoglycans — polysaccharides that contain amino sugars
Glycosaminoglycuronans — polysaccharides that contain amino sugars
and uronic acid moieties
Glycosaminolipids — lipids that contain amino sugars
Heparan sulfate — formerly called heparitin sulfate
Keratan sulfate — formerly called keratosulfate
CONTENTS OF OTHER VOLUMES
VOLUME IA
Chemistry of Amino Sugars
Edited by ROGER W. JEANLOZ
D. Hort on: Monosaccharide Amino Sugars
Gunnar Blix and Roger W. Jeanloz : Sialic Acids and Muramic Acid
H. H. Baer: Oligosaccharides
J. Strominger: Nucleotide Derivatives of Amino Sugars
R. U. Lemieux: Naturally Occurring Glycosides of Amino Sugars with Anti
biotic Activity
Bibliography and Author Index; Subject Index
VOLUME IB
Glycosaminoglyccins, Glycoproteins, and Glycosaminolipids
Edited by ROGER W. JEANLOZ and ENDRE A. BALAZS
PART I
Sven Gardell : Isolation and Separation of Glycosaminoglycans
Roger W. Jeanloz and Nathan Sharon : Chemical Structure of Glycosamino
glycans
T. C. Laurent and John Scott: Physical Structure of Glycosaminoglycans
PART II
Glycopeptides and Glycoproteins
Nathan Sharon: Glycopeptides from Bacterial Cell Wall
Karl Schmid : Glycoproteins from Blood Plasma
J. Montreuil : Glycoproteins from Various Tissues and Tissue Fluids
L. Odin and I. Werner: Glycoproteins from Epithelial Secretions
David Aminoff: Glycoproteins with Blood-Group Specificity
PART III
Glycosaminolipids
E. Lederer: Glycosaminolipids from Gram-positive Bacteria
0. Westphal and O. Lüderitz: Glycosaminolipids from Gram-negative
Bacteria
E. Klenk: Glycosaminolipids from Higher Plants and from Animals
PART IV
Methods of Determination and Localization
Sven Gardell: Separation and Determination of H exosamines, Sialic Acids,
and Muramic Acid
Endre A. Balazs: Histochemistry of Amino Sugar-Containing Compounds
Bibliography and Author Index; Subject Index
xvi!
xviii Contents of Other Volumes
VOLUME MA
Distribution and Biological Role
Edited by ENDRE A. BALAZS and ROGER W. JEANLOZ
Nathan Sharon: Distribution of Amino Sugars in Microorganisms,
Plants, and Invertebrates
Robert G. Spiro: Amino Sugars and Macromolecules Containing Amino
Sugars in Liver
Robert G. Spiro: Amino Sugars and Macromolecules Containing Amino
Sugars in Kidney
Norman F. Boas: Amino Sugar-Containing Compounds in Urine
Zacharias Dische: Amino Sugar-Containing Compounds in Mucuses and
in Mucous Membranes
I. Werner and L. Odin: Glycoproteins in Salivary Glands, Saliva, and
Sputum
R. H. Pearce: Glycosaminoglycans and Glycoproteins in Skin
B. Sylvén: Amino Sugar-Containing Compounds in Tumors
I. Werner and L. Odin: Amino Sugar-Containing Compounds in Patho
logical Effusions
Nils R. Ringertz: Glycosaminoglycans in Mast Cells and in Mast-Cell
Tumors
J. A. Szirmai: Glycosaminoglycans in Umbilical Cord
Lars Sundblad: Glycosaminoglycans and Glycoproteins in Synovial Fluid
J. A. Szirmai: Glycosaminoglycans in the Connective Tissue of the
Electric Organ
Maxwell Schubert and David Hamerman: Amino Sugar-Containing
Compounds in Cartilage, Tendon, and Intervertébral Disc
E. A. Balazs and H. J. Rogers: The Amino Sugar-Containing Compounds
in Bones and Teeth
Helen Muir: Glycosaminoglycans and Glycoproteins in Blood-Vessel
Walls
Richard J. Winzler: Glycoproteins and Glycosaminoglycans in Plasma
and in Some Other Body Fluids
Sen-itiroh Hakomori: Substances Containing Amino Sugars in Blood
Cells and in Hemopoietic Organs
Lars Svennerholm: Glycolipids and Other Amino Sugar-Containing Com
pounds in the Nervous System
E. A. Balazs: Amino Sugar-Containing Macromolecules in the Tissues
of the Eye and the Ear
Bibliography and Author Index; Subject Index
