The Peptides: Analysis and Synthesis. Volume 4

330 Pages·1981·5.845 MB·English

by  Erhard Gross

The Peptides volume 4
T HE P E P T I D ES
Analysis, Synthesis, Biology
Treatise Editors
E. GROSS AND J. MEIENHOFER
Volume 1
Major Methods of Peptide Bond Formation
Volume 2
Special Methods in Peptide Synthesis, Part A
Volume 3
Protection of Functional Groups in Peptide Synthesis
Volume 4
Modern Techniques of Conformational, Structural, and Configurational
Analysis
The
Peptides
Analysis, Synthesis, Biology
VOLUME 4 Modern Techniques of Conformational,
Structural, and Configurational Analysis
Edited by
ERHARD GROSS
National Institutes of Health
Bethesda, Maryland
JOHANNES MEIENHOFER
Chemical Research Department
Hoffmann-La Roche Inc.
Nutley, New Jersey
1981
ACADEMIC PRESS
A Subsidiary of Harcourt Brace Jovanovich, Publishers
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COPYRIGHT © 1981, BY ACADEMIC PRESS, INC.
ALL RIGHTS RESERVED.
NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR
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ACADEMIC PRESS, INC.
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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:
The Peptides.
Includes bibliographies and indexes.
CONTENTS: v. 1. Major methods of peptide bond forma
tion.—v. 2. Special methods in peptide synthesis,
part A. —v. 4. Modern techniques of peptide and
amino acid analysis.
1. Peptides. I. Gross, Erhard. II. Meienhofer,
Johannes. [DNLM: 1. Peptides. QU 68 P424 1979]
QP552.P4P47 574.19'245 78-31958
ISBN 0-12-304204-6 (v.4) AACR1
PRINTED IN THE UNITED STATES OF AMERICA
81 82 83 84 9 8 7 6 5 4 3 2 1
Contents
List of Contributors ix
Preface xi
Nomenclature and Abbreviations xiii
Contents of Previous Volumes xvii
Chapter 1
X-Ray Analysis: Conformation of
Peptides in the Crystalline State
Isabella L. Karle
I Introductory Remarks 1
II Cyclic Dipeptides 4
III Peptides Containing Tri-, Tetra-, and Pentapeptide
Rings 8
IV Hexapeptide and Heptapeptide Rings 14
V Cyclic Octapeptides to Pentadecapeptides 24
VI Linear Peptides 33
VII Geometry of the Peptide Unit 41
VIII Intramolecular Hydrogen Bonds 42
IX Summary 49
References 49
Chapter 2
Crystal Structure Analysis of the
Larger Peptide Hormones
Jennifer Gunning and Tom Blundell
I Introduction 55
II Insulin and Proinsulin 57
III Hormones Homologous to Insulin 68
ν
vi Contents
IV Glucagon 75
V Pancreatic Polypeptide 78
VI Placental and Pituitary Hormones 79
VII Conclusion and Outlook 81
References 82
Chapter 3 Determination of the Absolute
Configuration of α-Amino Acids
and Small Peptides by Chiroptical
Means
Voldemar Toome and Manfred Weigele
I Introduction 86
II Definitions: Optical Rotatory Dispersion and
Circular Dichroism 88
III Chiroptical Properties of Amino Acids 89
IV Chiroptical Properties of Metal Complexes and
Chromophoric Derivatives of a-Amino Acids 97
V Chiroptical Properties of Oligopeptides 151
VI Chiroptical Properties of Metal Complexes and
Chromophoric Derivatives of Di- and Oligopeptides 158
VII Solvent, Salt, and Temperature Effects 168
VIII Instrumentation 169
IX Calibration and Standards 171
X Conclusion and Outlook 173
References 173
Chapter 4 Ultramicroanalysis of Peptides
and Proteins by High-Performance
Liquid Chromatography and
Fluorescence Detection
Stanley Stein
I Introduction 186
II Detection 187
III High-Performance Liquid Chromatography 195
IV Applications 198
V Conclusion 212
References 214
Contents vii
Chapter 5 Amino Acid Analysis of Peptides
James R. Benson, Paul C. Louie, and
Ralph A. Bradshaw
I Introduction 217
II Historical 218
III Experimental 223
IV Concluding Remarks 255
References 256
Chapter 6 Solid-Phase Sequencing of
Peptides and Proteins
Richard A. Laursen
I Introduction 261
II Chemistry of the Edman Degradation 262
III Immobilization of Peptides 264
IV Supports 274
V Instrumentation 278
VI Sequencing Strategies 278
VII Scope and Limitations 280
References 281
Author Index 285
Subject Index 301
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List of Contributors
Numbers in parentheses indicate the pages on which the authors' contributions begin.
James R. Benson* (217), Dionex Chemical Corporation, Sunnyvale, California
94806
Tom Blundell (55), Laboratory of Molecular Biology, Department of Crystal
lography, Birkbeck College, University of London, London WC1E 7HX,
United Kingdom
Ralph A. Bradshaw (217), Department of Biological Chemistry, Washington
University School of Medicine, St. Louis, Missouri 63110
Jennifer Gunning (55), Laboratory of Molecular Biology, Department of Crys
tallography, Birkbeck College, University of London, London WC1E
7HX, United Kingdom
Isabella L. Karle (1), Laboratory for the Structure of Matter, Naval Research
Laboratory, Washington, DC 20375
Richard A. Laursen (261), Department of Chemistry, Boston University, Bos
ton, Massachusetts 02215
Paul C. Louie (217), Dionex Chemical Corporation, Sunnyvale, California
94806
Stanley Stein (185), Roche Institute of Molecular Biology, Nutley, New Jersey
07110
Voldemar Toome (85), Chemical Research Department, Hoffmann-La Roche
Inc., Nutley, New Jersey 07110
Manfred Weigele (85), Chemical Research Department, Hoffmann-La Roche
Inc., Nutley, New Jersey 07110
^Present address: Interaction Chemicals Inc., 800 Jordan Ave., Los Altos, California 94022
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