Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (vol. 10)

557 Pages·1979·38.77 MB·English

by  R. C. Sheppard

A Specialist Periodical Report
Amino-acids, Peptides, and
Proteins
Volume 10
A Review of the Literature Published
during 1977
Sen io r Rep0r ter
R. C. Sheppard, MRC Laborafory of Molecular Biology,
Cambridge
The Chemical Society
Burlington House, London, WIT ONB
British Library Cataloguing in Publication Data
Amino-acids, peptides and proteins.
Vol. 10. - (Chemical Society. Specialist periodical reports).
1. Amino acids 2. Peptides 3. Proteins
I. Sheppard, Robert Charles 11. Series
547’.75 QD431 72-92548
ISBN 0 85186 094 X
ISSN 03060004
Copyright @ 1979
The Chemical Society
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 retried systems - without
written permission from The Chemical Society
Reporters
E Atherton MRC Laboratory of Molecular W Marki F. Hoffmann-La Roche & Co.,
Biology, Cambridge Basle, Switzerland
K Ban kowski Medical College of Ohio, W D Mercer University of Leeds
Ohio, USA B A Morgan Reckitt & Colman Ltd., Hull
G C Barrett Oxford Polyfechnic M Oppliger Eidg. Technische Hoch-
D Brandenburg Deutsches Wollforschungs- schule, Zurich, Switzerland
insfitut, Aachen, Germany D J Osguthorpe University of
T Brittain University of East Anglia Manchesfer
B W Bycroft University of Noffingham R H Pain University of Newcastle upon
A Dell lmperial College of Science and Tyne
Technology, London M Rangarajan Imperial College of
D P E Dickson University of Liverpool Science and Technology , Lon don
K Do Eidg. Technische Hochschule, Zurich, H W E Rattle Portsmouth Polytechnic
Switzerland B Robson University of Manchesfer
A Eberle Eidg. Technische Hochschule, P D Roy Beecham Research Laboratories,
Zurich, Switzerland Befchworth, Surrey
A E Faruk University of Nottingham D Saunders Deutsches Wollforschungs-
J-L Fauchere Eidg. Technische Hochschule, insfitut, Aachen, Germany
Zurich, Switzerland W H Sawyer Columbia University,
W Fischli Eidg. Technische Hochschule, New York, USA
Zurich, Switzerland R Schwyzer Eidg. Technische Hoch-
B Gillessen F. Hofmann-La Roche & Co,, schule, Zurich, Switzerland
Basle, Switzerland A V Stachulski University of Oxford
A Hallett University of Oxford R M Stephens Portsmouth Polytechnic
R Harrison lmperial College of Science and R 0 Studer F. Hofmann-La Roche & Co.,
Technology, London Basle, Switzerland
J G Hoggett University of York P Thanei Eidg. Technische Hochschule,
V M Kriwacrek Eidg. Technische Hoch- Zurich, Switzerland
sch ule, Zurich, Switzerland R Thomas University of Newcastle upon
U Ludescher F. Hoffman-La Roche & Co., Tyne
Basle, Switzerland E J Wood University of Leeds
M Manning Medical College of Ohio, Ohio,
USA
Organic formulae composed by Wright’s Symbolset method
Pinted In Gred Britain by John Wright and Sons Ltd., ut The Stonebrfdgr Press, Bristol BS4 5NU
Preface
This tenth Report reviews papers relevant to the chemistry of amino-acids,
peptides, and proteins published in the main journals during 1977. As in previous
volumes, Reporters have been encouraged to include discussion of important
papers seen in current journals. This volume therefore also includes references to
the early 1978 literature and even to papers known to be in the press at the time of
writing. It is hoped that this will increase the topicality and value of the Report.
Chapter 5 includes a section on vasoactive peptides, a subject not covered in
Volume 9. This section therefore covers the literature for 1976 and 1977.
It is with great sadness that we record the deaths this year of two of the fore-
most and most respected British peptide and protein chemists. Dr. J. I. Harris
died in an accident in South Wales in April, and Professor G. W. Kenner died,
also under tragic circumstances, in North Wales in June. Both made major
contributions to the subject over a period of more than twenty-five years. Ieuan
Harris was one of the pioneering figures in the development and application of
sequencing methods to peptide hormones and proteins. His work included total
amino-acid sequence determination of several enzymes of more than 300 residues
and was carried out with a degree of thoroughness and double checking which
left little room for error. George Kenner was also a pioneering figure, but
primarily in the field of synthesis. His work was characterized by strict application
of the rigorous principles of organic chemistry which led him to favour solution
methods rather than the solid-phase approach. This Report includes discussion
of the philosophy and present status of his work on enzyme synthesis.
Ieuan Harris was 53 and George Kenner 56 years old. Both leave major
research programmes presently incomplete. More happily, this volume records
completion of a collaborative project, synthesis by Kenner and his colleagues of
the 34 amino-acid residue hormone big gastrin according to a sequence determined
by Harris and Runswick.
In another vein, it is a pleasure to thank once more all the many contributors to
this Report whose names are listed opposite.
R. C. SHEPPARD
Contents
Chapter I Amino-acids
By G. C. Barretf
1 Introduction 1
Textbooks and Reviews 1
2 Naturally Occurring Amino-acids 1
Occurrence of Known Amino-acids 1
New Natural Free Amino-acids 3
New Amino-acids from Hydrolysates 4
3 Chemical Synthesis and Resolution of Amino-acids 5
Asymmetric Synthesis 5
General Methods of Synthesis of a-Amino-acids 6
Prebiotic Synthesis ; Model Reactions 7
Protein and Other Naturally Occurring Amino-acids 8
a-Alkyl Analogues of the Protein Amino-acids 11
a-Alkoxy-, a-Alkylamino-, and Alkylthio- analogues of the
Protein Amino-acids 11
Side-chain Halogenated Analogues of the Protein Amino-
acids 11
Aliphatic Amino-acids Carrying Hydroxy-groups in Side-
chains 12
Amino-acids with Unsaturated Side-chains 12
Aromatic and Heterocyclic Amino-acids 13
N-Substituted Amino-acids 13
a-A za-amino-acids 14
a-Amino-acids containing Sulphur or Selenium 14
A list of Amino-acids which have been Synthesized for the
First Time 15
Labelled Amino-acids 15
Resolution of Amino-acids 16
4 Physical and Stereochemical Studies of Amino-acids 18
Crystal Structures of Amino-acids and their Derivatives 18
N.M.R. Spectroscopy 18
O.R.D. and C.D. Spectra 19
Mass Spectrometry 20
Other Physical and Theoretical Studies 21
vi Contents
5 Chemical Studies of Amino-acids 22
Racem iza tion 22
General Reactions 23
Specific Reactions of Individual Protein Amino-acids 25
Specific Reactions of Amino-acids Related to Biochemical
Processes 27
Effects of Electromagnetic Radiation on Amino-acids 27
6 Analytical Methods 28
Gas-Liquid Chromatography 28
Ion-exchange Chromatography 29
Thin-layer Chromatography 30
Other Separation Methods 31
Determination of Specific Amino-acids 31
Chapter 2 Structural Investigation of Peptides and Proteins
I A: Protein Isolation and Characterization
By R. Harrison
1 Introduction 33
2 Protein Isolation Methodology 33
Chromatography 33
General Comments on Ligand Affinity Chromatography 33
Choice of Matrix and Method of Attachment 35
Effect of Spacer between Matrix and Ligand 36
Choice of Ligand 36
Protein and Other Macromolecular Ligands 37
Choice of Eluant 37
The Use of Affinity Chromatography to Remove Un-
wanted Proteins 38
Immunoaffinity Chromatography 39
Lectin Affinity Chromatography 40
Heparin Affinity Chromatography 41
Hydrophobic Chromatography 41
Metal Chelate and Covalent Chromatography 42
Biospecific Elution from Non-affinity Ligands 42
Electrophoretic Procedures 43
Miscellaneous Procedures 43
Solubilization of Membrane Proteins 45
Multienzymq Preparations 45
3 Purification of some Specific Classes of Proteins 46
Lectins 46
Antibodies 46
Proteases 47
Cascade Enzymes of Serum 47
Contents vii
4 Tabulated Lists of Purifications 47
5 Protein Characterization Methodology 66
Protein Determination 66
Electrophoretic Characterization 67
Apparatus and Electrophoretic Support Media 67
Isoelectric Focusing 67
Slab Gels and Two-dimensional Separations 68
Sodium Dodecyl Sulphate Polyacrylamide Gel Electro-
phoresis 68
Immunochemical Techniques 69
Electrophoretic Characterization of Specific Classes of
Proteins 69
Staining Techniques 70
Molecular Weight Determination 71
Finger Printing of Proteins 71
6 Polyfunctional Chains and Multienzyme Complexes 72
1B : Protein Sequencing Methods
By M. Rangarajan
1 Chain Cleavage and Separation of Peptides 72
Cleavage at Tryptophan Residues 72
Enzyme cleavage at Arginine Residues 73
2 Detection of Peptides 74
Fluorescamine, o-Phthalaldehyde, and Ninhydrin 74
3 Amino-acid Analysis 74
4 End-group Determination 74
5 Spinning Cup Sequencing 76
6 Solid-phase Sequencing 77
7 Microsequencing 79
8 Phenylthiohydantoin Amino-acids 79
9 C-Terminal Sequencing 79
10 Mass Spectrometry 80
11 New Strategies in Protein Sequencing 81
12 Novel N-Terminal Amino-acids 106
13 Isopeptide Linkages in Proteins 106
viii Contents
1 C: Chemical Modification of Proteins
By A. Dell
1 Introduction 108
2 Re-investigation of Known Reagents and Reactions 154
Cyanide Treatment of Molybdenum Iron-Sulphur Flavin
H y drox ylases 154
Carbodi-imide 154
N-Bromosuccinimide 154
Photolysis of Tryptophan 154
As-3-Ketosteroid Isomerase 154
Iodination 154
Peroxidase-Iodide Oxidation 155
3 New Reagents and Techniques 155
4 Chemical Cross-linking 157
5 Photocross-linking 158
6 Photolabelling 161
7 Distant Reporter Group 161
8 Competitive Labelling 162
9 Afhity Labelling 162
Il: X-Ray Studies
By W. D. Mercer
1 Introduction 165
2 Equipment and Methods 169
3 Immunoglobulins 183
4 Electron Transport and Redox Reactions 184
Myoglobin 184
Haemoglobin 185
Cy tochromes 188
Rubredoxin 189
Flavodoxin 189
5 Lysozyme 190
Con tents ix
6 Proteolytic Enzymes 191
7 Glycolytic Enzymes 19 4
Phosphorylase a 194
Hexokinase 194
Glucose-6 -p hos p ha te Isomerase 195
Glyceraldehyde-3-phosphateD ehydrogenase 195
Pyruvate Kinase 196
Post Gycolytic Enzymes 196
Other Glycolytic Dehydrogenases 196
8 Other Globular Proteins 197
Adenylate Kinase 197
Dihydrofolate Reductase 198
W hea t-germ Agglutinin 199
Ferri t in 199
Arabinose-binding Protein 200
Miscellaneous 200
9 Protein Conformation 201
10 Muscle 204
11 Other Biological Structures 205
12 Fibrous Proteins 206
13 Membranes and Lipoproteins 207
14 Synthetic Peptides 207
Ill: Conformafion and Interaction of Peptides and
Proteins in Solution
Edited by R. H. Pain
1 Theoretical Aspects of Protein Conformation 208
Contributed by D. J. Osguthorpe and B. Robson
Solvent Behaviour 208
Protein and Polypeptide Behaviour 210
Improvement of Energy Functions 21 1
Protein Folding 212
Conclusions 214
2 Mechanisms of Folding in Globular Proteins 214
Contributed by R. Thomas
Stability 215
Thermodynamics 215
Stabilization against Denaturation 21 5