Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC))vol.23

338 Pages·1992·13.96 MB·English

by  J. H. Jones

A Specialist Periodical Report
Amino Acids and Peptides
Volume 23
A Review of the Literature Published
during 1990
Senior Reporter
J. H. Jones, University of Oxford
Reporters
G.C. Barrett, Oxford Polytechnic
J.S. Davies, University College of Swansea
D.T. Elmore, University of Oxford
C.H. Frydrych, Beecham Pharmaceuticals
R.W. Hay, University of St Andrews
K.B. Nolan, The Royal College of Surgeons in Ireland
ROYAL
CHEMISTRY
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ISBN 0-85 186-2 14-4
ISSN 0269-7521
@ The Royal Society of Chemistry. 1992
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Printed and bound in England by Bookcraft (Bath) Ltd
Preface
This is the tenth volume in this series which it has been my
privilege to co-ordinate, and I trust I will be forgiven for
stepping down. The need for literature digests in the area is
increasing all the time: the annual output on most topics has
more than doubled since volume 1 (1968 literature).
Unfortunately, this also makes the Reporters' work the more
daunting, and I would like to record with special warmth how
grateful I am to those who have soldiered on year after year so
willingly and authoritatively. Dr John Davies has been one of
these stalwarts (his help has been especially valuable in this
my last year, during which he has agreed to contribute not one
but two chapters), and I am glad to be able to hand over the
operation to him.
Balliol College, Oxford John Jones
Cont ents
Chapter 1 Amino Acids
By G C Barrett
1 Introduction 1
2 Textbooks and Reviews 1
3 Naturally Occurring Amino Acids 2
Isolation of Amino Acids from Natural
Sources 2
New Natural Amino Acids 3
New Amino Acids from Hydrolyzates 3
4 Chemical Synthesis and Resolution of Amino Acids 5
General Methods for the Synthesis of
a-Amino Acids 5
Asymmetric Synthesig of a-Amino Acids 10
Synthesis of Protein Amino Acids and Other
Naturally Occurring a-Amino Acids 17
a-Alkyl and Aryl Analogues of Protein Amino
Acids 22
a-Amino Acids Carrying Alkyl Side-Chains,
and Cyclic Analogues 23
Prebiotic Synthesis of Amino Acids 25
a -Alkoxy a-Amino Acids 26
Halogeno-alkyl a-Amino Acids 26
a-(U-Hydroxyalkyl) a-Amino Acids 27
a-Amino Acids Carrying Unsaturated
Side-chains 27
Aromatic and Heteroaromatic a-Amino Acids
N-Substituted a-Amino Acids 29
a-Amino acids containing Sulphur, Selenium,
or Tellurium 30
Phosphorus-Containing a-Amino Acids 30
Labelled Amino Acids 30
p- And Higher Amino Acids 33
Resolution of DL-Amino Acids 41
5 Physico-chemical Studies of Amino Acids 46
Crystal Structures of Amino Acids and Their
Derivatives 46
Nuclear Magnetic Resonance Spectrometry 46
Optical Rotatory Dispersion and Circular
Dichroism 48
Mass Spectrometry 48
Other Physico-chemical Studies 48
Molecular Orbital Calculations 51
Contents
6 Chemicals Studies
Racemization
General Reactions of Amino Acids
Specific Reactions of Amino Acids
7 Analytical Studies of Amino Acids
Gas-Liquid Chromatography
Ion-exchange Chromatography and Related
Techniques
Thin-layer Chromatography
High Performance Liquid Chromatography
Fluorimetric Analysis
Other Analytical Methods
Assays for Specific Amino Acids
References 71
Chapter 2 Peptide Synthesis
By D T Elmore
1 Introduction 89
2 Methods
Amino-group Protection
Carboxyl-group Protection
Side-chain Protection
General Deprotection
Peptide Bond Formation
Disulphide Bond Formation
Solid-phase Peptide Synthesis
Enzyme-mediated Synthesis and
Semi-synthesis 116
Miscellaneous Reactions Related to Peptide
Synthesis 120
3 Selected Examples of Peptide Synthesis 121
4 Appendix. A List of Syntheses 122
Natural Peptides, Proteins, Analogues and
Fragments 122
Sequential Oligo- and Poly-peptides 129
Enzyme Substrates and Inhibitors 130
Conformation of Synthetic Peptides 131
Glycopeptides 132
Phosphopeptides and Related Compounds 132
Immunogenic Peptides 133
Miscellaneous Peptides 133
5 Purification Methods 134
References 135
Chapter 3 Analogue and Conformational Studies on Peptide
Hormones and other Biologically Active Peptides 156
By J S Davies
1 Introduction 156
2 Peptide-backbone Modifications 156
y[CSNH]-Analogues (and retro-inverso
version ) 157
y[NHCO]-Retro-Inverso Analogues 157
Contents
y[CH2NH]-Amino Methylene Analogues (and
Retro-Forms) 159
y[CH=CH]- and v[CF=CH]-Ethylenic Isosteres 159
Phosphono-Peptides 160
Y[CH2CH2]-Carba Analogues 160
y[CH20]-Methyleneoxy Analogues 160
y[COO]-Depsipeptides 160
Replacement of L- by D-Residues 162
Miscellaneous Modifications 162
a,a-Dialkylated Glycine Analogues 162
3 Conformationally Restricted Cyclic and Bridged
Analogues 165
Rings and Bridges formed via Amide Bonds 166
Bridges formed by Disulfide Bonds 169
Miscellaneous Bridges and p-Turn Mimetics 170
4 Dehydroamino Acid Analogues 172
5 Enzyme Inhibitors 174
Angiotensin Converting Enzyme (ACE)
Inhibitors 174
Renin Inhibitors 175
Inhibitors of Other Enzymes 184
6 Side-chain Interactions Studied by Residue
Substitution or Deletion and Similar
Modifications 186
Peptides with 'Opioid Characteristics' 186
Cholecystokinin Analogues 190
Angiotensin and Analogues 191
Vasopressin Analogues 192
Luteinising Hormone-Releasing Hormone
( LHRH 193
Miscellaneous Examples 195
7 Conformational Information derived from
Physical Methods 200
Nuclear Magnetic Resonance and Related
Techniques 200
X-Ray Crystallography 202
Circular Dichroism/Theoretical and
Computational Methods 202
References 203
Chapter 4 Cyclic, Modified and Conjugated Peptides 211
By J S Davies
1 Introduction 211
2 Cyclic Peptides
Naturally occurring Dioxopiperazines
(Cyclic Dipeptides)
Other Dioxopiperazines
Cyclic Tetrapeptides
Cyclic Pentapeptides
Cyclic Hexapeptides
Cyclic Hepta and Octapeptides
Higher Cyclic Peptides
Contents
Peptides containing Thiazole Type Rings 224
Cyclodepsipeptides 225
Cyclic Peptides containing Other
Non-protein Ring Components 232
3 Modified Linear Peptides
Phosphonopeptides
4 Conjugate Peptides 238
Glycopeptide Antibiotics 238
Other Glycopeptides 241
Non-carbohydrate Peptide Conjugates 244
References 246
Chapter 5 P-Lactam Antibiotic Chemistry
By C H Frydrych
1 Introduction 249
2 New Natural Products 249
3 Biosynthesis 249
4 Penicillins and Cephalosporins 252
5 Clavulanic Acid and Oxapenams 258
7 Carbapenems, Carbacephems, and Related Systems 259
8 Azetidinones 263
Reactions in which One Bond is Formed 263
1-2 Bond-forming Reactions 263
3-4 Bond-forming Reactions 263
1-4 Bond forming Reactions 265
Reactions in which Two Bonds are Formed 267
-
[3+1] Additions 267
1-2 and 2-3 Bond Formation 267
-
[2+2] Additions 267
1-2 and 3-4 Bond Formation 267
1-4 and 2-3 Bond Formation 269
Chemistry of Azetidinones 271
Further Uses of Azetidinones 275
9 Major Structural Variants 275
10 Mechanistic Studies, Mode of Action, and
Degradation 281
Appendix: p-Lactam Antibiotics Prepared for
Structure-activity Relationships and
Miscellaneous p-Lactams 284
References 287
Chapter 6 Metal Complexes of Amino Acids and Peptides 297
By R W Hay and K B Nolan
1 Introduction 297
Con tents
2 Amino Acid Complexes
Synthesis and Structures
Reactions
Formation Constants
3 Peptide Complexes 319
Synthesis, Structure, and Reactivity 319
Formation Constants, Species in Solution 321
References 325
Abbreviations
Abbreviations for amino acids and their use in the formulation
of derivatives follow, with rare exceptions, the 1983
Recommendations of the IUPAC-IUB Joint Commission on Biochemical
Nomenclature, which are reprinted as an Appendix in Volume 16 of
this title. Exceptions and additions are defined in the text as
they occur.