Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (vol. 6)

532 Pages·1975·21.19 MB·English

by  R. C. Sheppard

A Specialist Periodical Report
Amino-acids, Peptides, and
Proteins
Volume 6
A Review of the Literature Published
during 1973
Senior Reporter
R. C. Sheppard, MRC Laborafory of Molecular Biology,
Camb ridge
ISBN : 0 85186 054 0
Library of Congress Catalog Card No. 7242548
@ Copyright 1975
The Chemical Society
Burlington House, London, WIV OBN
Reporters
G. C. Barrett, Oxford Polytechnic
J. Bridgen, MRC Laboratory of Molecular Biology, Cambridge
B. Byc roft, Universify of Noffingham
R. Cam ble, ICl Pharmaceuticals Division, Alderley Park, Macclesfield
E. A. Carrey, Universify of Newcastle
C. Chothia, lnstifuf Pasteur, Paris
A. S. Dutta, ICI Pharmaceuticals Division, Alderley Park, Macclesfield
A. T. Hagler, The Weizmann Insfifufe, Rehovof, Israel
C. E. Johnson, University of Liverpool
J. H. Jones, Universify of Oxford
P. Knowles, University of Leeds
G. L. E. Koch, MRC Laboratory of Molecular Biology, Cambridge
R. H. Pain, University of Newcasfle
G. R. Penrer, Universify of York
H. W. Rattle, Portsmouth Polyfechnic
B. Ridge, Universify of Exeter
B. Robson, University of Newcasfle
R. M. Stephens, Porfsmoufh Polytechnic
Organic formulae composed by Wright’s Symbolset method
PR1NTF.D IN GREAT BRlTAIN BY JOHN WRIGHT AND SONS LTD., AT THE STONEBRIDGE PRESS,B RISTOL
Preface
This sixth Report reviews papers relevant to the chemistry of amino-acids,
peptides, and proteins published in the main journals during 1973. Metal
derivatives are reviewed biennially in this series and are not included this
year. Likewise, next year’s Report will include reviews of circular di-
chroism and optical rotatory dispersion studies and association-dissocia-
tion reactions of proteins covering the literature for 1973 and 1974. The
other main areas surveyed this year are the same as those in Volume 5.
I thank most warmly the many contributors to this volume for their
time and effort devoted to its preparation.
R. C. SHEPPARD
Contents
Chapter 1 Amino-acids 1
By G. C. Barreff
1 Introduction
Textbooks and Reviews
2 Naturally Occurring Amino-acids
Occurrence of Known Amino-acids
New Natural Free Amino-acids
New Amino-acids from Hydrolysates
3 Chemical Synthesis and Resolution of Amino-acids 8
General Methods of Synthesis 8
Asymmetric Synthesis 8
Syntheses using a-Isocyano- and a-Isothiocyanato-
esters 9
Syntheses by Classical Methods 11
Synthesis under Simulated Prebiotic Conditions 13
Protein and Other Naturally Occurring Amino-acids 14
a-Alkyl- and a-Aralkyl-a-amino-acids 15
a-Hydroxy-a-amino-acids and Amino-acids with
Aliphatic Hydroxy-groups in the Side-chain 15
Aromatic and Heterocyclic Amino-acids 16
N-Substituted Amino-acids 17
Amino-acids containing Sulphur 18
a-Amino-acids which have been Synthesized for the
First Time 19
Amino-acids with Amino-alkyl Side-chains 20
Labelled Amino-acids 20
Resolution of Amino-acids 22
4 Physical and Stereochemical Studies of Amino-acids 23
Crystal Structures of Amino-acids 23
N.M.R. Spectrometry 24
O.R.D. and C.D. Spectra 25
Combined Use of Physical Methods; Amino-acid
Derivatives in Solution 26
Mass Spectrometry 27
Determination of Absolute Configuration 28
vi Contents
5 Chemical Studies of Amino-acids 28
Racemization and Inversion 28
General Reactions 29
Specific Reactions and Interactions 30
Effects of Electromagnetic Radiation on Amino-acids 32
6 Analytical Methods 33
Gas-Liquid Chromatography 33
Ion-exchange and Partition Chromatography 35
Th in-1a yer and Paper Chromatography 36
Other Analytical Methods 37
Determination of Specific Amino-acids 38
Chapter 2 Structure Investigation of Peptides and Proteins 39
I: Primary Sfructure and Chemical Modification
By J. Bridgen and G. L. E. Koch
1 Introduction 39
2 Protein Isolation and Characterization 39
Techniques for Isolating Proteins 39
Affinity Chromatography 42
Estimation of Protein Concentration 47
Molecular Weight Determination 48
3 Chemical Modification 78
Methods 78
Thiol Groups 78
Methionine 79
Tyrosine 79
Amino-groups 79
Carboxy-groups 79
Iodination 80
Fluorescent Labelling 80
Cross-linking Reagents 81
General Applications 81
Affinity Labelling 81
Immunoglobulins 81
Ribosomal Proteins 94
Aminoacyl-tR NA Synt hetases 95
Isomerases 95
Dihydrofolate Reductase 96
Lysozyme 96
Aspartate Aminotransferase 96
Photoaffinit y Labelling 96
Cont ents vii
Immunoglobulins 96
RNA Polymerase 98
Subtilisin 99
Cross-linking 101
Ribosomal Proteins 101
Erythrocyte Membranes 103
Haemoglobin 103
Coenzyme Analogues 103
NAD 103
ATP 104
AMP 1 04
4 Methods 105
Fragmentation 105
Aminopeptidases 105
Carboxypeptidase 105
Di- and Tri-peptidases 105
Chemical Fragmentation 106
Fractionation 106
Amino-acid Analysis 108
Sample Preparation 108
Buffer Systems 108
Unusual Amino-acids 109
Capillary Analyser 109
Integration of Results 109
Fluorescamine 109
Gas-Liquid Chromatography 111
0t her Met hods 112
Terminal Group Identification 112
Sequence Analysis 112
Sequencer 114
Solid-phase Sequencing 115
Identification of Hydantoins 117
Mass Spectrometry 118
Glycopeptides 118
5 Partial Sequences 118
Amino-terminal Sequences 121
Immunoglobulins 121
Proteinases 124
Other Proteins 127
Sequences around Reactive Residues 130
Cysteine Sequences 130
Serine Sequences 132
0t her Residues 133
...
Vlll Contents
6 Complete Sequences 134
Muscle Proteins 134
Actin 134
Parvalbumins 135
Troponin C 135
Structural Proteins 135
Wool Proteins 135
Proteases and Protease Inhibitors 137
Trypsin 137
Trypsin Inhibitor 137
Nucleases 137
Ribonuclease 137
Deoxyrib onuclease 139
Venom Proteins 139
Immunoglobulins 141
Peptides and Hormones 142
Hypothalamic Pep tides 146
Miscellaneous 147
Subtilin 147
Tentoxin 147
Redox Proteins 147
Cytochrome c 147
Flavodoxins 149
Globins 150
Hb Mutants 150
Chromosomal Proteins 152
Histones 152
Protamines 153
Miscellaneous 153
Carbonic Anhydrases 153
Glutamate Dehydrogenase 154
Tryptophan Sy nt het ase 154
a,-Acid Glycoprotein 155
/&Microglobulin 155
/I: X-Ray Studies 163
By C. Chofhia
1 Introduction 163
2 Amino-acids and Peptides 163
Lithium Antamanide and Sodium [Phe4,Val]"Anta-
manide Complexes 165
Con tents ix
3 Low-resolution Studies of Proteins 166
Fibrous Proteins 166
Collagen 166
a-Keratin 166
Low-angle X-Ray Scattering by Proteins in Solutioh 168
The Unit Cell and Symmetry of New Crystals of
Globular Proteins 168
Low-resolution Studies of Globular Proteins 168
Aspartate Transcarbamylase (ATCase) 168
Hexokinase 173
Adenylate Kinase 173
Alkaline Phosphatase 173
4 High-resolution Studies of Globular Proteins 174
Immunoglo bins 174
Electron Transport Proteins 177
Structure of Cytochrome cz and c550 177
Conformational Changes on Oxidation or Reduc-
tion of Cytochrome c 179
Bacterial Ferredoxin 181
Rubredoxin 183
Bacterial Flavodoxin 183
Carp Muscle Calcium-binding Protein (Myogen) 183
Haemoglobins 187
Haemoglobin M Boston 188
Haemoglobin Yakima 189
Haemoglobin Little Rock 190
Haemoglobin Seattle 190
Haemoglobin S 191
Haemoglobin from Sea Lamprey 191
Enzymes of the Glycolytic Pathway 191
~-Glyceraldehyde-3-phosphatDee hydrogenase 191
Liver Alcohol Dehydrogenase 194
Yeast Phosphoglycerate Kinase 195
Lactate Dehydrogenase 195
Hydrolytic Enzymes 198
Bovine Trypsin - Bovine Pancreatic Trypsin
Inhibitor Complex 198
Comparison of the Crystal Structures of Chymo-
trypsinogen A and a-Chymotrypsin 200
a-Chymotrypsin 200
Ribonuclease 202
Lysozyme 202