Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 3)

397 Pages·1971·31.68 MB·English

by  J. S. Davies

A Specialist Periodical Report
Amino-acids, Peptides, and
Proteins
Volume 3
A Review of the Literature Published
during 1970
Senior Reporter
G. T. Young, The Dyson Perrins Laboratory, University
of Oxford
SBN: 85186 024 9
@ Copyright 1971
The Chemical Society
Burlington House, London, WIV OBN
Reporters
C. C. F. Blake, University of Oxford
J. R. Brocklehurst, University of Oxford
B. W. Bycroft, University of Noftingham
D. G. Dalgleish, University of Oxford
J. S. Davies, University College of Swansea, University of Wales
R. D. Gillard, University of Kent
R. Henson, University of Oxford
J. H. Jones, University of Oxford
S. H. Laurie, Leicesfer Polytechnic
P. H. Lloyd, University of Oxford
A. R. Peacocke, University of Oxford
R. Perham, Cambridge University
N. C. Price, University of Oxford
R. M. Stephens, Portsmouth Polytechnic
J. 0. Thomas, Cambridge University
Organic fnrmulue composed by Wright's Symbolset Method
PRINTED IN GREAT BRITAIN BY JOHN WRIGHT AND SONS LTD., AT THE STONEBRIDGE PRESS, BRISTOL
-
This third Report continues in the pattern of the earlier volumes, reviewing
papers relevant to the chemistry of amino-acids, peptides, and proteins
appearing in the main journals in 1970; in all, some 2300 references are
quoted. The unfortunate cessation of publication of Current ChemicaZ
Papers has made systematic coverage more difficult, and we shall be grateful
if our attention is drawn to any important omissions in the bibliography;
some December issues of journals were delayed by the postal strike, and
references from these journals will be included in the next volume. It will
be recalled that the extent of new work on metal derivatives was considered
insufficient for annual review and this field was not covered in Volume 2;
Chapter 5 therefore surveys this literature for 1969 and 1970. Work on the
synthesis of cyclic peptides, formerly appearing in Chapter 3 (Peptide
Synthesis) is now included in Chapter 4 (Peptides with Structural Features
Not Typical of Proteins), in which structural work on such peptides is
discussed. We would draw attention to the collected references now a
feature of several chapters, e.g. the list of amino-acids whose syntheses were
first reported during the year (Chapter l), the list of peptide syntheses, and
the (selective) list of new intermediates useful in synthesis (Chapter 3). We
would remind readers that extracts relevant to this field from the Tentative
Rules of the 1.U.P.A.C.-I.U.B. Commission on Biochemical Nomenclature
were reprinted in Volume 2.
As in earlier volumes, there is an author index but instead of a subject
index (the preparation of which would delay publication unduly) there is an
extended list of contents; an inspection of this will, we hope, enable the
reader to see readily which sections are likely to contain the material he
seeks.
Once more I record my gratitude to the contributors who have taken
time from their research to produce this survey for their colleagues in the
field.
G. T. YOUNG
Contents
Chapter 1 Amino-acids
w.
By B. Bycroff
1 Naturally Occurring Amino-acids
A Introduction
B New Natural Free Amino-acids
C New Amino-acids from Peptide Hydrolysates
D Occurrence of Known Amino-acids
2 Chemical Synthesis and Resolution of Amino-acids 5
A Introduction 5
B Protein and Other Naturally Occurring Amino-
acids 8
C C-Alkyl- and Substituted C-Alkyl-a-amino-acids 8
D a-Amino-acids with Aliphatic Hydroxy-groups in
the Side-chain 9
E Aromatic and Heterocyclic a-Amino-acids 10
F N-Alkyl-a-amino-acids 11
G a-Amino-acids containing Sulphur or Selenium 12
H A List of a-Amino-acids which have been Syn-
thesised for the First Time 13
I Labelled Amino-acids 14
J Resolution of a-Amino-acids 15
3 Physical and Stereochemical Studies of Amino-acids 15
A Determination of Absolute Configuration 15
B Crystal Structures of Amino-acids 16
C Optical Rotatory Dispersion (0.r.d.) and Circular
Dichroism (c.d.) 17
D Nuclear Magnetic Resonance (n,m.r.) Spectra 18
E Mass Spectrometry 18
F Other Physical and Stereochemical Studies 19
4 Chemical Studies of Amino-acids 19
A Oxidation and Reduction 19
B General Reactions 21
C Specific Reactions 23
D Non-enzymic Models of Biochemical Processes
Jnvolving Amino-acids 24
E Effects of Electromagnetic Radiation on Amino-
acids 26
vi Contents
5 Analytical Methods 28
A Gas-Liquid Chromatography 28
B Ion-exchange Chromatography 29
C Thin-layer Chromatography 29
D Other Methods 30
E Determination of Specific Amino-acids 30
Chapter 2 Structural Investigation of Peptides and Proteins
I Primary Structures and Chemical Modification
By R. N. Perham and J. 0. Thomas
1 Introduction 31
2 Methods 32
A Amino-acid Analysis 32
Ion-exchange Chromatography 33
High-voltage Electrophoresis and Thin-layer
Chromatography 34
Gas-Liquid Chromatography 35
B End-group Analysis and Sequential Degradation 35
C Mass Spectrometry 39
D Cleavage of Protein Chains 43
Enzymic Cleavage 44
Restriction of Enzymic Cleavage 44
Chemical Cleavage 45
Tnsolubilised Enzymes 48
E Fractionation Methods 49
Chromatography 49
Electrophoresis 51
Peptide Detection and Identification 53
Affinity Chromatography 54
3 Structural Proteins 58
A The Proteins of Motility 58
B Collagen 60
Primary Structure 60
Cross-links 62
C Fibrinogen 63
D Chromosomal Proteins 64
E Miscellaneous 66
Serum and Egg Proteins 66
Milk Proteins 67
Virus Proteins 68
0t her Proteins 69
Contents vii
4 Peptides and Hormones 71
A Pancreatic Hormones 71
B Pituitary Hormones 71
C Other Hormones 75
D Kinins, Encephalitogenic Protein, and Toxins 77
E Peptide Antibiotics 78
5 Enzymes 79
A Proteolytic Enzymes 79
B Lysozyme and a-Lactalbumin 89
C Ribonucleases 92
D Dehydrogenases 94
E Other Enzymes 98
F Haem Proteins 107
Haemoglobin and Myoglobin 107
Cytochrornes 109
G Non-haem Electron Transport Proteins 110
H Studies on Quaternary Structure 111
6 Immunoglobulins 114
A Light Chains 114
B Heavy Chains 117
C Disulphide Bridges 119
D Antibody Binding Sites 120
E Some Implications for Biosynthesis 122
7 Membrane Proteins 123
A Red Blood Cell Membranes 124
B Mitochondria1 and Other Membranes 126
8 Chemical Modification 127
A Amino-groups 127
Anhydrides 127
Other Reagents 128
Introduction of Thiol Groups by Substitution at
Amino-groups 129
B Carboxy Groups 130
C Thiol Groups 131
D Tyrosine 132
Nitration 132
Iodination 133
Acetylation and Other Methods 134
E Tryptophan, Histidine, and Arginine 134
F Photo-oxidation 137
G Active-site-direct ed Inhibitors 139
...
Contents
Vlll
I1 X-Ray Studies
By C. C. F. Blake
1 Introduction 139
2 Amino-acids and Oligopeptides 140
A Arginine 140
B Histidine 140
C 0-Phosphoryl-serine 140
D Valine 140
E Perdeuterio-a-gly cyl gl ycine 141
3 Proteins 141
A Methods 141
B Results 142
a-Chymotrypsin 142
Chymotrypsinogen 145
Elastase 147
Haemoglobin 150
Erythrocruorin 159
Rubredoxin 159
Lactate Dehydrogenase 160
Ribonuclease S 162
Preliminary Data for Other Proteins 162
Ill Spectroscopic and Solution Studies on the Conformation
and Interactions of Polypeptides and Proteins
Edited by A. R. Peacocke
1 Introduction 164
2 Infrared 165
Contributed by R. M. Stephens
3 Optical Rotatory Dispersion and Circular Dichroism 168
Contributed by D. G. Dalgleish
A General 168
B Amino-acids and Synthetic Polypeptides 168
C Small Peptides 172
D Haem Proteins 173
E Binding of Small Molecules to Proteins 175
F Modified Proteins 176
G Denaturation and Unfolding 178
H Lipoproteins and Membranes 179
I Protein-Nucleic Acid Interactions 181
J Proteins 182
Contents ix
4 Nuclear Magnetic Resonance 185
Confribufed by R. Henson
A General 185
B Amino-acids 186
C Peptides 188
D Histones 190
E Hormones and Peptide Antibiotics 191
F Non-iron-containing Proteins 193
G Iron Proteins 195
H Nuclei other than Hydrogen 197
I Conclusion 199
5 Fluorescence 199
Confribufed by J. R. Brocklehursf
6 Spin Labels 205
Contribufed by N. C. Price
A Measurements of Correlation Time 205
B Interaction of the Unpaired Electron with Neigh-
bouring Paramagnetic Ions or Nuclei 208
C Interaction of the Unpaired Electrons in a Biradical 209
7 Dissociation and Association of Proteins 210
Contributed by P. H. Lloyd
Chapter 3 Peptide Synthesis
By J. H. Jones
1 Introduction 219
2 Methods 22 1
A Protective Groups 221
Established Methods of Amino-group Protection 221
New Methods of Amino-group Protection 224
Miscellaneous Publications on Amino-group
Protection 224
Protection of Carboxy-groups 225
Protection of Hydroxy-groups 226
Protection of Primary Amide Groups 226
Protection of Arginine Side-chains 227
Protection of Thiol Groups and Synthesis of
Cystine Peptides 228
B Formation of the Peptide Bonds 23 1
Activated Esters 23 1
X Contents
Coupling Methods involving Dicyclohexyl-
car bodi-imide 234
Other Methods 235
C Purification of Synthetic Intermediates 237
D Racemisation 238
E Repetitive Methods of Peptide Synthesis 243
Solid-phase Synthesis 243
0t her Methods 247
F Synthesis of Polymeric Models for Studies in Pro-
tein Chemistry 248
Polyamino-acids 248
Sequential Polypeptides 249
G Synthetic Operations with Peptides of Biological
Origin 250
With Naked Natural Peptides 250
With Partially Blocked Peptides 252
3 Syntheses Achieved and Structure-Activity Correlations 252
A Calcitonin 253
B Cholecystokinin-pancreozymin 254
C RibonucIease Systems 256
D Staphylococcal Nuclease Systems 257
E [4-Threonine]-Oxytocin 259
F Thyroid-stimulating Hormone Releasing Factor 261
4 Appendix A: A List of Syntheses Reported during 1978 263
A Naturally Occurring Peptides, Proteins, Analogues,
and Partial Sequences 263
B Sequential Polypeptides 268
E Miscellaneous Peptides 269
5 Appendix B: A List of Some Useful New Synthetic
Intermediates Described during 1978 270
6 Appendix C: Some Recent Applications of Hydroxy-
propylated Dextran (Sephadex LH-20) in Peptide
Chemistry 274
Chapter 4 Peptides with Structural Features Not Typical of
Proteins
By J. S. Davies
1 Introduction 276
2 Cyclic Peptides 277
A 2,5-Dioxopiperazines 279