Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC))vol.18

316 Pages·1987·2.12 MB·English

by  J. H. Jones

Amino Acids and Peptides
Volume 18

A Specialist Periodical Report
Amino Acids and Peptides
Volume 18
A Review of the Literature Published
during 1985
Senior Reporter
J. H. Jones, University of Oxford
Reporters
G. C. Barrett, Oxford Polytechnic
J. Brennan, UMlST
J. S. Davies, University College of Swansea
1. J. Galpin, University of Liverpool
P. M. Hardy, University of Exeter
R. W. Hay, University of Stirling
K. B. Nolan, University of Surrey
A. Sheppard, UMlST
The Royal Society of Chemistry
Burlington House, London WlV OBN
ISBN 0-851 86- 164-4
ISSN 0269-7521
Copyright 01 987
The Royal Society of Chemistry
All Rights Reserved
No part of this book may be reproduced or transmitted in any form
or by any means - graphic, electronic, including photocopying, recording,
taping, or information storage and retrieval systems - without
written permission from the Royal Society of Chemistry
Printed in Northern Ireland at The Universities Press (Belfast) Ltd.
Preface
Our syllabus and approach are as in the previous volume, but we
have been obliged to submit to the discipline of producing
camera-ready copy for the first time. The formulae have been
drawn €or us by the R.S.C., but the layout of the text has been
our own responsibility. Some of us are novices at this art
form, and crave indulgence accordingly.
The most notable relevant book' published during 1985 is edited
by our colleague John Davies. It is largely a derivative work,
drawn from the 1982 edition of the 'Dictionary of Organic
Compounds', but the entries have all been reviewed and updated
where necessary, and some three hundred completely new ones have
been added. There are getting on for two thousand all told, and
perhaps ten thousand literature citations. The compilation,
which is arranged alphabetically, gives physical, chemical, and
bibliographic data on all the important amino acids and
peptides. The amino acids of proteins have very full entries,
and their principal protected derivatives also appear
individually. The rarer amino acids are covered as well,
together with nearly all known dipeptides; higher peptides are
listed if they are of biological or pharmaceutical importance.
Coverage extends not only to peptide antibiotics, including
6-lactams, but also to natural products such as the peptide
alkaloids.
A number of valuable monographs have appeared on biological
aspects of amino acid and peptide chemistry. Although aimed at
advanced biomedical students, readers of this Report will also
find them useful as introductory background reading. Bender's
well-known 'Amino Acid Metabolism'* is now out in a second
edition. Wallis, Howell, and Taylor's 'The Biochemistry of the
Polypeptide Hormones'3 has a chapter on each main class of peptide
vi Amino Acids and Peptides
hormone and will be very helpful to any chemist entering tne
will
field. So 'Immun~logy'b~y Roitt, Brostoff, and Male,
which is remarkable €or its profuse, clear, and elegant
diagrams.
Balliol College, Oxford John Jones
July 1986
References
1. 'Amino Acids and Peptides', ed. J.S. Davies, Chapman and Hall Ltd., 1985.
2. D.A. Bender, 'Amino Acid Metabolism', 2nd Edn., John Wiley and Sons Ltd.,
1985.
3. M. Wallis, S.L. Howell, and K.W. Taylor, 'The Biochemistry of the
Polypeptide Hormones', John Wiley and Sons Ltd., 1985.
4. I. Roitt, J. Brostoff, and D. Male, 'Immunology', Gower Medical Publishing
Ltd., 1985.
Cont ents
Chapter 1 Amino Acids
By G. C. Barrett
1 Introduction
2 Textbooks and Reviews
3 Naturally Occurring Amino Acids
Occurrence of Known Amino Acids
New Natural Amino Acids
New Amino Acids from Hydrolysates
4 Chemical Synthesis and Resolution of
Amino Acids 4
General Methods of Synthesis 4
5
Asymmetric Synthesis
Prebiotic Synthesis Models 6
Synthesis of Protein Amino Acids and Other
Naturally Occurring a-Amino Acids 6
Synthesis of 13- and Higher Homologous
10
Amino Acids
Synthesis of a-Alkyl Analogues of Protein
Amino Acids 10
Synthesis of Other Aliphatic and Alicyclic
Analogues of Protein Amino Acids 12
Synthesis of a-Alkoxy-a-Amino Acids and
Related a-Heteroatom Substituted
a-Amino Acids 12
Synthesis of Halogenoalkyl Amino Acids 12
Synthesis of Aliphatic Amino Acids
Carrying Side-chain Hydroxy Groups 13
Synthesis of Aliphatic Amino Acids with
Unsaturated Side Chains 13
Synthesis of Amino Acids with Aromatic or
Heterocyclic Side-chain Groupings 16
Synthesis of Amino Acids with Side Chains
Containing Sulphur or Selenium 16
Amino Acids Synthesized for the First Time 17
Synthesis of Labelled Amino Acids 17
Resolution of DL-Amino Acids 19
5 Physical and Stereochemical Studies of
Amino Acids 21
Crystal Structures of Amino Acids and
Their Derivatives 21
Nuclear Magnetic Resonance Spectrometry 21
viii Amino Acih and Peptides
Optical Rotatory Dispersion and Circular
Dichroism 24
Mass Spectrometry 24
Other Physical Studies 25
Molecular Orbital Calculations 26
6 Chemical Studies of Amino Acids 27
Racemization of Amino Acids 27
General Reactions of Amino Acids 27
Specific Reactions of Amino Acids 31
Non-enzymic Models of Biochemical Processes
Involving Amino Acids 35
Effects of Electromagnetic Radiation on
Amino Acids 36
7 Analytical Methods 36
Gas-Liquid Chromatography 36
Ion-exchange Chromatography 37
Thin-layer Chromatography 38
High-performance Liquid Chromatography 38
Fluorescence Methods 40
Other Methods 40
Determination of Specific Amino Acids 40
References 41
Chapter 2 Peptide Synthesis
By I. J. Galpin, with Appendices compiled
by C. M. Galpin
1 Introduction 57
2 Methods 58
Protective Groups 58
Established Methods of Amino-group
Protection 58
New Methods of Amino-group Protection 61
Carboxyl Protection 62
Side-chain Protection 64
General Deprotection 66
Formation of Peptide Bonds 68
Racemization 78
Repetitive Methods of Peptide Synthesis 80
Enzyme-mediated Synthesis and Semi-
synthesis 88
3 Synthesis 91
4 Appendix I: A List of Syntheses Reported
in 1985 96
Natural Peptides, Proteins, and Partial
Sequences 96
Sequential Oligo- and Poly-peptides 104
Enzyme Substrates and Inhibitors 105
Glycopeptides 107
Miscellaneous Peptides 107
5 Appendix 11: Amino Acids Derivatives Useful
in Synthesis 109
Coded Amino Acids 110
Uncoded Amino Acids 111
Contenb ix
6 Appendix 111: Purizication Methods 113
High-performance Liquid Chromatography 113
Gas-Liquid Chromatography 114
Other Chromatographic Methods 114
References 114
Chapter 3 Analogue and Conformational Studies on Peptide
Hormones and Other Biologically Active
Pepti d e s
By J. S. Davies
1 Introduction 140
2 Peptide-backbone Modifications 140
y[CSNH] Analogues 140
,[NHCO] Retro-Inverso Analogues 14 2
y[CONR] N-Alkylated Analogues 14 3
y[CH NH] Aminomethylene Analogues 143
Replicement of L-Res idues by D-Res idues 14 3
a,a-Dialkylated Glycine Analogues 14 4
3 Conformationally Restricted Bridged Analogues 14 5
Somatostatin 14 5
Enkephalins 14 5
Bradykinin 14 6
Carba Analogues of Oxytocin and Vasopressin 14 6
Other Cyclic Analogues 14 6
4 Dehydroamino Acid Analogues 148
5 Enzyme Inhibitqrs 149
Angiotensin Converting Enzyme (ACE)
Inhibitors 14 9
Renin Inhibitors 152
Other Types of Inhibitors 153
6 Side-chain Interactions Studied by Residue
Substitution or Deletion, and Related
Modifications 154
7 Conformational Information Derived from
Physical Methods 157
Nuclear Magnetic Resonance Studies 157
X-Ray and Related Techniques 160
Infrared and Circular Dichroism Studies 162
Computational Methods 163
References
164
Chapter 4 Cyclic, Modified, and Conjugated Peptides
By P. M. Hardy
1 Introduction 169
2 cyclic Peptides 169
Dioxopiperazines (Cyclic Dipeptides) 169
Cyclic Tri- to Hexa-peptides 177
Larger Cyclic Peptides 182
Cyclic Depsipeptides 186
Other Cyclic-Peptides with Modified Backbones 187