Amino Acids, Peptides and Proteins [Splst Period'l Rpt Vol 11]

572 Pages·1981·31.58 MB·English

Am ino-acids, Peptides,
and Proteins
Volume 1 I
A Specialist Periodical Report
Amino-acids, Peptides, and
Proteins
Volume 11
A Review of the Literature Published
during I978
Senior Reporter
R. C. Sheppard, MRC Laboratory of Molecular Biology,
Cambridge
The Royal Society of Chemistry
Burlington House, London W1 V OBN
British Library Cataloguing in Publication Data
Amino-acids, peptides, and proteins.-
(Royal Society of Chemistry. Specialist periodical reports).
Vol. 11
1. Amino acids 2. Peptides 3. Proteins
I. Sheppard, Robert Charles 11. Series
547’.75 QD43 1 72-92548
ISBN 0-85 186-880-0
ISSN 0306-0004
Copyright o 198 1
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 inf ormation
storage and retrieval systems - without written permission from The Royal Society of
Chemistry
Reporters
G C Barrett Oxford Polytechnic
D Bra nd enb u r g D eutsches Wollforschungsinst itut, A achen,
Germany
T Brittain University of Auckland, Auckland, Newzealand
f E Cohen University of Oxford
D H Coy Department of Medicine, Tulane University, Louisiana, USA
A DelI Imperial College of Science and Technology
0 P E Dickson University of Liverpool
I J Galpin University of Liverpool
M F J Galpin University of Liverpool
D Gillessen F. Hofmann-LaR oche & Co., Basel, Switzerland
R Harrison Children’s Hospital Medical Center, Boston,
Massachusetts, USA
R W Hay University of Stirling
M Kruszynski Medical College of Ohio, Toledo, Ohio, USA
M Manning MedicalCollege of Ohio, Toledo, Ohio, USA
W D Mercer Queen’s University of Belfast, Belfast, Northern Ireland
R H Pain University of Newcastle upon Tyne
M Rangarajan Imperial College of Science and Technology
H W E Rattle Portsmouth Polytechnic
P D Roy Oce-Andeno B. V., Venlo, Holland
6- E Rudolph Deutsches Wollforschungsinstitut, Aachen, Germany
D Saunders Deutsches Wollforschungsinstitut, Aachen, Germany
W H Sawyer Department of Pharmacology, Columbia University,
New York USA
P W Schiller Clinical Research Institute of Montreal, Quebec,
Canada
R M Stephens Portsmouth Polytechnic
M J E Sternberg University of Oxford
R 0 Studer F. Hoffmann-La Roche & Co., Basel, Switzerland
R M Thomas University of Newcastle upon Tyne
D R Williams University of Wales Institute of Science and
Technology, Cardiff
E J Wood University of Leeds
Printed in Great Britain by Henry Ling Ltd, at the Dorset Press, Dorchester, Dorset
Preface
This eleventh Report reviews papers relevant to the chemistry of amino-acids,
peptides, and proteins published in the main journals during 1978. Subject
coverage is similar to that of previous volumes except that the usual chapter on
peptides with structural features not typical of proteins has unfortunately had
to be omitted.
Chapter 4 dealing with chemical structure and biological activity is selective
rather than comprehensive. The present volume includes the biennial survey of
metal derivatives of amino-acids, peptides, and proteins.
It is a pleasure once more to thank the many contributors to this volume
whose names are listed opposite.
R. C. SHEPPARD
Contents
Chapter 1 Amino-acids
By G. C. Barrett
1 Introduction
Textbooks, Reviews, and General Articles
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 5
General Methods of Synthesis of a-Amino-acids 5
Synthesis of@-Amino-acidsa nd Higher Homologues 7
Asymmetric Synthesis 7
Prebiotic Synthesis; Model Reactions 8
Protein Amino-acids and Other Naturally Occurring
Amino-acids 9
Aliphatic Amino-acids 11
a-Alkyl Analogues of Protein Amino-acids 11
a-Hetero-atom Substituted a-Amino-acids 11
a-Halogenoalkyl-a-amino-acids 11
Aliphatic Amino-acids Carrying Hydroxy-groups in
Side-chains 11
a-Amino-acids with Unsaturated Side-chains 12
Aromatic and Heterocyclic Amino-acids 12
N-Substituted Amino-acids 13
n-Amino-acids Containing Sulphur 13
A list of Amino-acids which have been Synthesized for the
First Time 14
Labelled Amino-acids 14
Resolution of Amino-acids 15
4 Physical and Stereochemical Studies of Amino-acids 17
Crystal Structures of Amino-acids and Their Derivatives 17
N.M.R. Spectrometry 18
Optical Rotatory Dispersion and Circular Dichroism 20
Mass Spectrometry 2 0
Other Physical and Theorefical Studies 2 1
...
v~ll Contents
5 Chemical Studies of Amino-acids 23
Racemization 2 3
General Reactions 24
Specific Reactions of Natural Amino-acids 25
Specific Reactions of Amino-acids Related to Biochemical
Processes 26
Effects of Electromagnetic Radiation on Amino-acids 27
6 Analytical Methods
Gas-Liquid Chromatography
Ion-exchange Chromatography
Thin-layer and Paper Chromatography
High Performance Liquid Chromatography
Fluorimetry
Other Separation Methods
Determination of Specific Amino-acids
Chapter 2 Structural Investigation of Peptides and Proteins
/A :P rotein Isolation and Characterization 34
By R. Harrison 3 4
1 Introduction 3 4
2 Protein Isolation Methodology 34
General Comments on Isolation Methodology 34
Ligand Affinity Chromatography 36
General Comments 36
Choice of Matrix, Ligand, and Method of Ligand
Immobilization 3 7
The Influence of a Spacer between Ligand and Matrix 39
Optimum Conditions for Binding and Elution 39
Specific Ligands 40
Anthraquinone Dyes 40
Nucleic Acids 41
Immunoglobulins 41
Hydrophobic Chromatography 42
Covalent Chromatography 42
Biospecific Elution from Ion-exchange Resins 43
Electrophoretic Procedures 4 3
Solubilization of Membrane Proteins 43
Miscellaneous Procedures 44
Contents ix
3 Tabulated Summaries of Selected Purifications 45
Ligands with Widespread Application - Table 1 48
Specific Affinity Ligands - Table 2 54
Miscellaneous Chromatographic Procedures - Table 3 62
4 Protein Characterization Methodology
Protein Determination
Electrophoretic Procedures
Isoelectric Focusing
Sodium Dodecyl Sulphate Polyacrylamide Gel Electro-
phoresis
Miscellaneous Electrophoretic Procedures
Two-dimensional Electrophoretic Separation of Proteins
Immunochemical Techniques
Peptide Mapping
Detection of Peptides and Proteins
Amino-Acid Composition
Molecular Weight Determination
IB: Protein Sequencing Methods
By M, Rangarajan
1 Chain Cleavage and Separation of Peptides 76
Cleavage at y-Carboxy-glutamic Acid Residues 76
Cleavage at Cysteine Residues 76
Cleavage of Pyroglutamic acid from the N-Terminus 77
Enzyme Cleavage at Proline Residues 79
2 Detection of Peptides 79
Fluorescamine, o-Phthalaldehyde and Ninhydrin 79
3 Amino-acid Analysis 80
4 End-group Determination 8 1
5 Spinning Cup Sequencing 84
6 Solid-phase Sequencing 8 6
7 Microsequencing 88
8 Phenylthiohydantoin Amino-acids 88
X Contents
9 C-Terminal Sequencing 90
10 Mass Spectrometry 9 1
11 New Strategies in Protein Sequencing 92
lC: Chemical Modification of Proteins
ByA. Dell
1 Re-investigation of Known Reagents and Reactions 156
Phenylmercuric Acetate 156
GI yoxal 156
Methyl Acetimidate 156
2,3-Dioxo-5-indoline Sulphonic Acid 156
2-Hydroxy-5-nitrobenzyl Bromide 156
P-Elimination of P-Halo Substrates by D-Amino-acid
Transaminase 156
Halogenation 156
Sulphonyl Fluorides 157
Cupric-o-phenanthroline Complex 157
3-Bromo- 1, 1 ,I -trifluoropropanone 157
2 Synthetic Procedures for Radiolabelled Reagents 157
3 New Reagents and Techniques 158
4 Chemical Cross-linking 160
6 Competitive Labelling 164
7 Affinity Labelling 165
I/:X -Ra y Studies
By W 0.M ercer
1 Introduction 168
2 Equipment and Methods
Equipment and Crystal Growth
Contents
General Methods
Structure Refinement
Structure Storage and Computer Graphics
3 Immunoglobulins and Lectins
Immunoglobulins
Concanavalin A
4 Oxygen-carrying and Electron Transport Proteins
Haem-protein Chemistry
Myoglobin
Haemoglobin
Haemerythrin
Erythrocruorin
Cytochromes
Cytochrome c Peroxidase
Thioredoxin
Rubredoxin
Azurin
Plastocyanin
5 Lysozyme
6 Proteolytic Enzymes and Ribonuclease
Trypsin and Trypsinogen
Chymotrypsin
Elastase
Streptomyces Protease A
Endothia Protease
Acid Proteases
Ribonuclease
7 Glycolytic Enzymes
Phosphorylase a
Phosphorylase b
Hexokinase
6-Phosphogluconate Dehydrogenase
Triose Phosphate Isomerase
Pyruvate Kinase
Alcohol Dehydrogenase