Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC))vol.16

431 Pages·1985·27.07 MB·English

by  J. H. Jones

Amino Acids, Peptides,
and Proteins
Volume 16
A Specialist Periodical Report
Amino Acids, Peptides,
and Proteins
Volume 16
A Review of the Literature Published
during 1983
Sen io r R epo rter
J. H. Jones, University of Oxford
Reporters
A. Atkinson, PHLS Centre for Applied Microbiology and Research, Porton
Down, Wiltshire
D. J. Barlow, Birkbeck College, University of London
G. C. Barrett, Oxford Polytechnic
J. 0. Baum, Birkbeck College, University of London
S. H. Bell, University of Liverpool
T. Brittain, University of Auckland, Auckland, New Zealand
R . Cassels, Beecham Pharmaceuticals, Epsom, Surrey
S. Craig, University of Newcastle upon Tyne
D. P. E. Dickson, University of Liverpool
M. L. J. Drummond, Birkbeck College, University of London
A. Electricwala, PHLS Centre for Applied Microbiology and Research, Porton
Down, Wiltshire
. .
J L F i n ne y, Birkbeck College, University of London
I. J. Gal pin, University of Liverpool
A. J. Garman, Beecham Pharmaceuticals, Epsom, Surrey
P. M. Hammond, PHLS Centre for Applied Microbiology and Research, Porton
Down, Wiltshire
(continued overleaf 1
The Royal Society of Chemistry
Burlington House, London WIV OBN
ISBN 0-85 186-144-X
ISSN 0306-0004
Copyright 0 1985
The Royal Society of Chemistry
All Rights Keserved
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
Reporters (continued)
P. M. Hardy, University of Exeter
P. D. Jeffrey, Australian National University, Canberra, Australia
A. Mathews, University of Auckland, Auckland, New Zealand
W. D. Mercer, Queen’s University of Belfast
L. W. Nichol, Australian National University, Canberra, Australia
R. H. Pain, University of Newcastle upon Tyne
M. D. Scawen, PHLS Centre for Applied Microbiology and Research, Porton
Down, Wiltshire
R. F. Sherwood, PHLS Centre for Applied Microbiology and Research, Porton
Down, Wiltshire
J. C. Smith, Birkbeck College, University of London
R. A. G. Smith, Beecham Pharmaceuticals, Epsom, Surrey
R. M. Stephens, Portsmouth Polytechnic
J. M. Thornton, Birkbeck College, University of London
D. J. Winzor, University of Queensland, Queensland, Australia
Set by Unicus Graphics Ltd, Horsham, West Sussex
and printed in Great Britain
by Whitstable Litho Ltd, Whitstable, Kent
Preface
This sixteenth Report reviews papers published during 1983 that are relevant to
the chemistry of amino acids, peptides, and proteins. The content and format
generally follow those of Volume 15. No chapter on Inorganic Aspects appears,
because it has been customary to review this sector in alternate years only.
Coverage of Primary Structure proved impossible to arrange, as did the
inclusion of separate subsections devoted to Nuclear Magnetic Resonance and
Fluorescence. These gaps are obviously unsatisfactory features, which give us
pain. Despite the gaps and an increasingly (excessively, even) compressed style
we have still exceeded our allocation of pages, and it has become clear that uYe
have been fighting a losing battle in our efforts to deal rapidly and exhaustively
with a relentlessly expanding volume of literature. The present Report is the last
that will attempt to review such a broad front. Its successor will concern itself
more specifically with the chemistry of amino acids and peptides - a retrograde
step, we admit, but inevitable. The field of review established in the early
Reports in the series has grown beyond containment in a single volume without
self-defeating selectivity and crowding.
One of the most important publications to appear during the year was the
report of the 1.U.P.A.C.-I.U.B. Joint Commission on Biochemical Nomenclature
giving its 1983 recommendations for amino acid and peptide nomenclature and
symbolism. Those who have thrashed out these recommendations with such
patience and meticulous attention to detail have done the subject a great service.
Whilst we make no claim to complete innocence from the occasional aberration
ourselves, we urge everyone in the field to conform.
Balliol College, Oxford JOHN JONES
November 1984
V
Cont ents
Chapter 1 Amino Acids
By G. C. Barrett
1 Introduction 1
Textbooks and Reviews 1
2 Naturally Occurring Amino Acids 1
Occurrence of Known Amino Acids 1
New Natural Amino Acids 2
New Amino Acids from Hydrolysates 3
3 Synthesis of Amino Acids 4
General Methods 4
Asymmetric Synthesis of Amino Acids 5
Models for Prebiotic Synthesis of Amino Acids 6
Synthesis of Protein Amino Acids and Other Naturally
Occurring &-AminoA cids 7
Synthesis of 0- and Higher Homologous Natural
Amino Acids 10
a-Alkyl Analogues of Natural &-Amino Acids 10
Synthesis of Other Aliphatic, Alicyclic, and Saturated
Heterocyclic Amino Acids 12
Synthesis of a-Alkoxy-a-amino Acids 14
Synthesis of Halogenoalkyl Amino Acids 14
Synthesis of Aliphatic Amino Acids Containing Side-
chain Hydroxy Groups 14
Synthesis of Aliphatic Amino Acids Containing Un-
saturated Side Chains 14
Synthesis of Aromatic and Heteroaromatic Amino
Acids 15
Synthesis of Amino Acids Containing Sulphur 15
Synthesis of Phosphorus-containing Amino Acids 16
Amino Acids Synthesized for the First Time 16
Synthesis of Labelled Amino Acids 17
Resolution of Amino Acids 18
4 Physical and Stereochemical Studies of Amino Acids 20
Crystal Structures of Amino Acids and Their Deriva-
tives 20
Nuclear Magnetic Resonance Spectrometry 21
vii
...
Vlll Contents
Optical Rotatory Dispersion and Circular Dichroism 22
Mass Spectrometry 23
Other Physical Studies 24
Molecular-orbital Calculations 26
5 Chemical Studies of Amino Acids 27
Racemization 27
General Reactions 28
Specific Reactions of Natural Amino Acids and Their
Derivatives 32
Non-enzymic Models of Biochemical Processes In-
volving Amino Acids 36
Effects of Electromagnetic Radiation on Amino Acids 36
6 Analytical Methods 37
Gas-Liquid Chromatography 37
Ion-exchange Chromatography 38
Thin-layer Chromatography and Related Techniques 38
High-perf ormance Liquid Chromatography 39
Fluorescence Methods 41
Other Methods 42
Determination of Specific Amino Acids 42
Chapter 2 Structural Investigations of Peptides and Proteins
lA: Protein Isolation and Characterization
By M. D. Scawen, A. Atkinson,
A. Electricwala, P. M. Hammond,
and R. F. Sherwood
1 Introduction 43
2 Protein Isolation Methodology 43
Affinity Chromatography 43
Coupling Techniques 43
Dye-affinity Chromatography 52
Hydrophobic-interaction and Covalent Chromato-
graphy 52
Hydrophobic-interaction Chromatography 52
Covalent Chromatography 53
Immunoaffinity Chromatography 53
Phase Partition 56
High-performance Liquid Chromatography 57
Other Chromatographic Techniques and Applications 58
C o n t e 12 t s ix
3 Isolation of Specific Classes of Proteins 59
Membrane Proteins 59
Plasma Proteins 71
4 Electrophoretic Techniques 71
One-dimensional Electrophoresis 71
Two-dimensional Electrophoresis 72
Isoelectric Focusing 72
Affinity and lmmunoelectrophoresis 72
Isotachophoresis 73
Protein Determination in Electrophoretic Gels 73
IB: Chemical Modification of Proteins
By R. Cassels, A. J. Garman,
and R. A. G. Smith
1 Introduction 74
2 Investigations of Known and Novel Reagents and Reactions 136
Te tranitromethane 136
Diethylenetriamine Penta-acetic Anhydride 136
5,5' -Dithiobis-(2-nitrobenzoic Acid) 136
Di-isopropyl Phosphorofluoridate 136
Other Reagents 136
3 Modifications for Physical Techniques 137
4 Crosslinking 141
5 Affinity Labelling 142
Nucleotide-binding Sites 142
Receptors 143
Enzyme Active Sites 143
6 Photoaffinity Labelling and Pho tocrosslinking 145
7 Mechanism-based Inhibitors 148
11: X-Ray Studies
By W. D. Mercer
1 Introduction 150
2 Crystallographic Theory and Methods 156
Theory and Methods 156
Equipment 157
X Contents
Data Processing and Collection 158
Protein Crystallographic Techniques 159
Structure Refinements 159
Computer Graphics 160
3 Immunoglobulins 160
Bence-Jones Protein, Rhe 160
Immunoglobulin G 161
4 Oxygen- and Electron-carryingP roteins 161
Haemoglobin 161
Haemeryth rin 162
Flavodoxin 162
Ferredoxin 163
Plastocyanin 163
Azurin 163
Cytochrome c 163
Flavocytochrome bz 164
Cytochrome c Complexes 164
5 Lysozymes and Ribonucleases 164
Lysozymes 164
Bovine Pancreatic Ribonuclease 165
Bacillus in termed ius Ribonuclease 165
6 Proteolytic Enzymes 165
Trypsin 165
Trypsin Inhibitor 166
Kallikrein 166
Carboxypeptidase A 167
Thermolysin 167
Streptomyces griseus Protease B 167
Penicillopepsin 167
Renin 168
7 Glycolytic and Tricarboxylic Acid Cycle Enzymes 168
Glycogen Phosphorylase 168
6-Phosphogluconate Dehydrogenase 169
Glyceraldehyde-3-phosphateD ehydrogenase 169
Alcohol Dehydrogenase 169
Malate Dehydrogenase 170
8 Hormones 170
Insulin 170