Table Of ContentChemistry
and Biological Activities
of Bacterial Surface Amphiphiles
Edited by
GERALD D. SHOCKMAN
Department of Microbiology and Immunology
Temple University School of Medicine
Philadelphia, Pennsylvania
ANTHONY J. WICKEN
School of Microbiology
University of New South Wales
Sydney, Australia
ACADEMIC PRESS 1981
A Subsidiary of Harcourt Brace Jovanovich, Publishers
New York London Toronto Sydney San Francisco
COPYRIGHT © 1981, 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.
Ill Fifth Avenue, New York, New York 10003
United Kingdom Edition published by
ACADEMIC PRESS, INC. (LONDON) LTD.
24/28 Oval Road, London NW1 7DX
Library of Congress Cataloging in Publication Data
Main entry under title:
Chemistry and biological activities of bacterial surface
amphiphiles.
Papers presented at a workshop held in New Orleans,
La., Jan. 12-16, 1981.
Includes index.
1. Microbial lipids—Congresses. 2. Microbial
polysaccharides—Congresses. 3. Cell membranes—
Congresses. I. Shockman, Gerald D. II. Wicken,
Anthony J. III. Title: Bacterial surface amphiphiles.
QR92.L5C48 589.9'019247 81-15023
ISBN 0-12-640380-5 AACR2
PRINTED IN THE UNITED STATES OF AMERICA
81 82 83 84 9 8 7 6 5 4 3 2 1
CONTRIBUTORS
Numbers in parentheses indicate the pages on which the authors' contributions begin.
Benjamin Appelbaum (341), Department of Microbiology, and Center for
Oral Health Research, School of Dental Medicine, University of Penn-
sylvania, 4001 Spruce Street, Philadelphia, Pennsylvania 19104
Lois Argenbright (69), Department of Microbiology, School of Dental
Medicine, University of Pennsylvania, 4001 Spruce Street, Philadelphia,
Pennsylvania 19104
Michael Bat ley (125), School of Chemistry, Macquarie University,
New South Wales, Australia
Edwin H. Beachey (315), The Veterans Administration Medical Center, and
The University of Tennessee College of Medicine, Memphis, Tennessee
Gary K. Best (263), Department of Cell and Molecular Biology, Medical Col-
lege of Georgia, Augusta, Georgia
Arnold S. Bleiweis (43), Department of Microbiology and Cell Science,
University of Florida, Gainsville, Florida
W. H, Bo wen (353), National Caries Program, National Institute of Dental
Research, National Institutes of Health, Bethesda, Maryland
Vicky M. Brautigan* (151), Department of Biochemistry and Molecular
Biology, Northwestern University, Evanston, Illinois
Gary B. Calandra (271), Laboratory of Streptococcal Diseases, National In-
stitute of Allergy and Infectious Diseases, National Institutes of Health,
Bethesda, Maryland
Erlinda Cabacungan (167), Department of Biochemistry, Temple University
School of Medicine, Philadelphia, Pennsylvania
Daniel D. Carson (259), Department of Microbiology and Immunology, Tem-
ple University School of Medicine, Philadelphia, Pennsylvania
Yu-hua U. Chen (327), Department of Microbiology and Immunology,
University of California, Berkeley, California
Warren C. Childs ///t (151), Department of Biochemistry and Molecular
Biology, Northwestern University, Evanston, Illinois
J. E. Ciardi (353), National Caries Program, National Institute of Dental
Research, National Institutes of Health, Bethesda, Maryland
^Present address: Seattle University, Seattle, Washington
^Present address: University of Illinois at the Medical Center, Chicago, Illinois
ix
χ Contributors
George C. Clark (327), Department of Microbiology and Immunology,
University of California, Berkeley, California
Ronald C. Craig (43), Department of Oral Biology, University of Michigan,
Ann Arbor, Michigan
Lolita Daneo-Moore (259), Department of Microbiology and Immunology,
Temple University School of Medicine, Philadelphia, Pennsylvania
Barry A. Fiedel (305), Department of Immunology/Microbiology, Rush
Medical Center, Chicago, Illinois
Franz Fiedler (195), Lehrstuhl für Mikrobiologie der Universität München,
D-8000 Munich, Federal Republic of Germany
Werner Fischer (181, 209), Institut für Physiologische Chemie, Universität
Erlangen-Nürnberg, Erlangen, Federal Republic of Germany
Mong-Ching W. Ganfield (167), Department of Biochemistry, Temple Univer-
sity School of Medicine, Philadelphia, Pennsylvania
Luis Glaser (137), Department of Biological Chemistry, Division of Biology
and Biomedical Sciences, Washington University School of Medicine, St.
Louis, Missouri 63110
Michael R. Gold (327), Department of Microbiology and Immunology,
University of California, Berkeley, California
Evan Güstow (167), Department of Biochemistry, Temple University School
of Medicine, Philadelphia, Pennsylvania
R. H. Haller (353), National Caries Program, National Institute of Dental
Research, National Institutes of Health, Bethesda, Maryland
Jeri L. Hill (327), Department of Microbiology and Immunology, University
of California, Berkeley, California
Stanley Holt (341), Department of Microbiology, University of
Massachusetts, Amherst, Massachusetts
Eskin Huff (79), Laboratory of Streptococcal Diseases, National Institute of
Allergy and Infectious Diseases, National Institutes of Health, Bethesda,
Maryland
Vincent J. Iacono (51), Department of Periodontics, School of Dental
Medicine, State University of New York at Stony Brook, Stony Brook,
New York
Jacob N. Israelachvili (119), Department of Applied Mathematics, Research
School of Physical Sciences, Institute of Advanced Studies, The
Australian National University, Canberra, ACT, Australia
Robert W. Jackson (305), Department of Medical Microbiology and Im-
munology, Southern Illinois University School of Medicine, Carbon-
dale, Illinois
Laura I. Katona (51), Department of Oral Biology and Pathology, School of
Dental Medicine, State University of New York at Stony Brook, Stony
Brook, New York
Robert E. Kessler (239), Dental Research Institute, The University of
Michigan, Ann Arbor, Michigan
Contributors xi
Kenneth W. Knox (I, 11, 89, 95, 229, 299), Institute of Dental Research,
Sydney, Australia
H. Uwe Koch (181), Institut für Physiologische Chemie, Universität Erlangen-
Nürnberg, Erlangen, Federal Republic of Germany
Elaine Kwan (327), Department of Microbiology and Immunology, University
of California, Berkeley, California
David A. Lee (327), Department of Microbiology and Immunology, Universi-
ty of California, Berkeley, California
Sang-hee Lim (101), Department of Microbiology, New York University
School of Medicine, New York, New York 10016
Otto Lüderitz (41), Max-Planck-Institut für Immunbiologie, Freiburg, Federal
Republic of Germany
Maclyn McCarty (239), The Rockefeller University, New York, New York
Robert I. Mishell (327), Department of Microbiology and Immunology,
University of California, Berkeley, California
Edward H. Montgomery (279), Department of Pharmacology, University of
Texas Health Science Center, Dental Branch, Houston, Texas
Francis C. Neuhaus (151), Department of Biochemistry and Molecular
Biology, Northwestern University, Evans ton, Illinois
Itzhak Ofek (315), Department of Human Microbiology, Tel Aviv University
School of Medicine, Tel Aviv, Israel
Nicolle Packer (125), School of Chemistry, Macquarie University, New South
Wales, Australia
Ronald A. Pieringer (167), Department of Biochemistry, Temple University
School of Medicine, Philadelphia, Pennsylvania
Jerry J, Pollock (51), Department of Oral Biology and Pathology, School of
Dental Medicine, State University of New York at Stony Brook, Stony
Brook, New York
John Redmond (125), School of Chemistry, Macquarie University, New South
Wales, Australia
J. A. Reilly (353), National Caries Program, National Institute of Dental
Research, National Institutes of Health, Bethesda, Maryland
Gunnar R0lla (353, 365), Dental Faculty, University of Oslo, Oslo, Norway
Burton Rosan (69, 340), Department of Microbiology, School of Dental
Medicine, University of Pennsylvania, 4001 Spruce Street,
Philadelphia, Pennsylvania 19104
Milton R. J. Salton (101), Department of Microbiology, New York University
School of Medicine, New York, New York 10016
David F. Scott (263), Department of Cell and Molecular Biology, Medical Col-
lege of Georgia, Augusta, Georgia
Gerald D. Shockman (21, 51, 247, 381), Department of Microbiology and Im-
munology, Temple University School of Medicine, Philadelphia,
Pennsylvania
xii Contributors
W. Andrew Simpson (315), The Veterans Administration Medical Center, and
The University of Tennessee College of Medicine, Memphis, Tennessee
Hutton D. Slade (113), Department of Oral Biology, University of Colorado
Health Sciences Center, Denver, Colorado
Theodore S. Theodore (276), Laboratory of Streptococcal Diseases, National
Institute of Allergy and Infectious Diseases, National Institutes of
Health, Bethesda, Maryland
Robert R. White (279), Department of Microbiology, University of Texas
Health Science Center, Dental Branch, Houston, Texas
Anthony J. Wicken (I, 11, 89, 95, 229, 247, 299, 381), School of
Microbiology, University of New South Wales, Sydney, Australia
William Wong (247), Department of Microbiology and Immunology, Temple
University School of Medicine, Philadelphia, Pennsylvania
Ivo van de Rijn (239), The Rockefeller University, New York, New York
PREFACE
This volume is a collection of the papers presented at a workshop held in
New Orleans, Louisiana, January 12, 1981, entitled Chemistry and Biological
Activities of Bacterial Surface Amphiphiles. While workshops, symposia, and
conferences devoted to the oldest known bacterial amphiphile, lipopolysac-
charide, have been numerous, this was the first time that newer amphiphiles,
particularly those of gram-positive bacteria, were considered in depth.
This workshop was conceived several years ago as a result of many discus-
sions between the organizers of the symposium (and the editors of this volume)
and others, many of whom were ultimately participants and contributors. It
was generally agreed that an interchange of physical, chemical, and biological
information on the newer amphiphiles would be timely and useful for future,
productive research. The goals set for the workshop were to review current
knowledge of bacterial amphiphiles, to consider and possibly standardize ap-
proaches to testing for biological activities of amphiphiles, to set guidelines for
criteria of purity of amphiphile preparations used in biological testing, to
determine major future avenues in amphiphile research, and to foster future
cooperative research in the field.
Achievement of these goals was attempted through the formal presentations
that appear in this volume as well as extensive and wide-ranging discussions.
Although it did not prove possible to present sensible and comprehensible
summaries of the many discussions, a distillation of these discussions, in the
form of recommendations for future research, is included as a final chapter in
this volume.
It was perhaps inevitable, given the wealth of data that has accumulated
over the past decade as well as the research interests of the organizers, that a
large portion of the workshop was devoted to one class of amphiphile, the
lipoteichoic acids. However, the principles and guidelines that emerged will be
of interest and assistance in research into the properties of other classes of
bacterial amphiphiles.
Both the organizers and participants were concerned with the complexity of
the interactions of amphiphiles with bacterial and mammalian cells and their
products,and concluded that to better understand these complexities, greater
interaction with biologists, on the one hand, and with chemists and physicists,
on the other, was needed. It is our hope that both the workshop and this
volume will help to increase such cooperative interaction.
xiii
xiv Preface
All workshops need a sponsor, and the national origins of the organizers of
this workshop were a happy combination, which resulted in obtaining
generous sponsorship under the United States-Australia Agreement for Scien-
tific and Technical Cooperation. Grateful acknowledgment is made to the Na-
tional Science Foundation in the United States and the Department of Science
and the Environment in Australia for both the financial aid and advice that
made this workshop possible. Support from Smith, Kline & French
Laboratories, Becton Dickinson & Co., and Pharmacia Fine Chemicals is also
gratefully acknowledged. Finally, the editors are greatly indebted to the par-
ticipants for their efforts in making possible this published account of their
presentations.
Gerald D. Shockman
Anthony J. Wicken
CHEMICAL COMPOSITION AND PROPERTIES
OF AMPHIPHILES
ι
Anthony J. Wicken
School of Microbiology
University of New South Wales
Sydney, Australia
2
Kenneth W. Knox
Institute of Dental Research
Sydney, Australia
I. INTRODUCTION
Amphiphiles or amphipathic molecules are characterized
by having both hydrophobic and hydrophilic regions in their
structure and are common to all cellular membranes, the
various classes of membrane lipids and some proteins for
example fall within this definition. In the context of this
collection of papers, however, the term amphiphile is used to
describe a chemically diverse range of bacterial polymers
that share certain physico-chemical as well as biological
properties that have proven or potential roles in the
pathogenesis of mammalian disease (1). While these
amphiphiles are membrane polymers they share varying degrees
of locational mobility (see G.D. Shockman, elsewhere this
volume) that may be of significance in their interactions
with mammalian tissues or systems. This paper reviews the
known types of bacterial amphiphile with respect to their
structure and properties.
Supported by the National Health and Medical Research
Council of Australia and Public Health Service grant R01
DE04175 from the National Institute of Dental Research.
2
Supported by the National Health and Medical Research
Council of Australia and Public Health Service grant R01
DE04174 from the National Institute of Dental Research.
Chemistry and Biological Activities Copyright © 1981 by Academic Press, Inc.
of Bacterial Surface Amphiphiles 1 All rights of reproduction in any form reserved.
ISBN 0-12-640380-5
2 Anthony J. Wicken and Kenneth W. Knox
LIPOPOLYSACCHARIDE
LLIIPPIIDD AA
O-POLYSACCHARIDE CCOORREE
(p ) (coo ).
LIPOPROTEIN
LLIIPPIIDD
POLYPEPTIDE
ENTEROBACTERIAL COMMON ANTIGEN
((NNAAccGGIIcc--NNAAccMMaannCCOOOOHH)) LLIIPPIIDD
nn
(FA)
LIPOTEICHOIC ACID
n( G LYCOSYL)POLYGLYCERO PHOSPHATE GLYCOLIPID
L
Ρ Ala (FA)2 -4
LIPOMANNAN
POLYMANNOSE LIPID
Succinyl
ACTINOMYCES AMPHIPHILE
jj LLIIPPIIDD
(Man, Glc, Gal)
n
Ρ Ala Lys (FA)
Fig. 1. Schematic re-presentation of known and proposed
structures of various classes of bacterial arrrphiphile. The
