Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 28)

393 Pages·1997·25.33 MB·English

by  J.S. Davies

Amino Acids, Peptides and Proteins
Volume 28
A Specialist Periodical Report
Amino Acids, Peptides
and Proteins
Volume 28
A Review of the Literature Published during 1995
Senior Reporter
J.S. Davies, University of Wales, Swansea, UK
Reporters
G.C. Barrett, Oxford, UK
S. C.G . Biagini, University of Wales, Bangor, UK
D.T. Elmore, University of Oxford, UK
J.A. Littlechild, University of Exeter, UK
M. North, University of Wales, Bangor, UK
C.J . Schof ield, University of Oxford, UK
J. E. Thirkettle, University of Oxford, UK
M.W. Walter, University of Oxford, UK
P. J. Williams, University of Wales, Bangor, UK
CHEMISTRY
Information
Services
ISBN 0-85404-212-1
ISSN 0269-7521
0T he Royal Society of Chemistry 1997
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Preface
We have reached an age when genetic engineering can generate orphan receptors
awaiting suitable ligands to be discovered, bringing us to the era of inverse
pharmacology. Prion proteins and their conformational changes are on their way
to being acclaimed as the source of BSE and CJD and other diseases of the
ageing process. Yet researchers in these fields complain that the lack of physical
techniques to identify the modified prions is hampering developments. So as all
our Reporters in this series once more report expansion and consolidation within
their areas, we can only hope that amongst the hard work put into the original
research, reported in 1995, there are developments which will assist in catching up
with the increased demands at the frontiers. The strides taken in applying
physical techniques to protein folding seem to be well advanced in this direction.
To bring together another compilation of published papers has again depended
on long hours of dedication from my fellow reporters, listed on the title page of
this book. The core of stalwart reporters from previous volumes remain a core
source of Chapter reviews for this volume as well, and we welcome back
Dr. Chris Schofield and his Oxford colleagues for their biennial look at the p-
lactam scene, which is under continuous evolution in trying to win the battles
against the microbes’ wish to survive. Topics in Chapter 3 recently have been
ably reviewed for us by Michael North and colleagues at Bangor. Due to other
calls on his ‘reviewing’ time, Michael is withdrawing from the team for the next
volume, but does so with much appreciation for his support for the series.
Two Peptide Symposia on the American (Columbus, Ohio) and European
(Edinburgh) sides of the Atlantic have taken place since the appearance of
Volume 27 in this series, and the books of Proceedings from them will serve as
hors-d’oeuvres to await the appearance of full papers from which our Reports are
compiled.
Once again, my sincere thanks go to my co-authors, and book editors at the
RSC at Cambridge under the watchful eye of Janet Freshwater. It is their effort
that has been instrumental in ensuring the continuation of this series into yet
another volume - Diolch yn fawr.
John S. Davies
University of Wales, Swansea
V
Contents
Chapter 1 Amino Acids
By Graham C. Barrett
1 Introduction
2 Textbooks and Reviews
3 Naturally Occurring Amino Acids
3.1 Isolation of Amino Acids from Natural Sources
3.2 Occurrence of Known Amino Acids
3.3 New Naturally Occurring Amino Acids
3.4 New Amino Acids from Hydrolysates
4 Chemical Synthesis and Resolution of Amino Acids
4.1 General Methods for the Synthesis of a-Amino
Acids
4.2 Asymmetric Synthesis of a-Amino Acids
4.3 Synthesis of Protein Amino Acids and other
Naturally Occurring a-Amino Acids
4.4 Synthesis of a-Alkyl Analogues of Protein Amino
Acids
4.5 Synthesis of a-Amino Acids Carrying Alkyl
Side-Chains, and Cyclic Analogues
4.6 Models for Prebiotic Synthesis of Amino Acids
4.7 Synthesis of a-Alkoxy a-Amino Acids and
Analogous a-Hetero-atom Substituted
a-Amino Acids
4.8 Synthesis of a-(a-Halogenoalkyl) a-Amino Acids
4.9 Synthesis of a-(a-Hydroxyalky1)-a-Amino Acids
4.10 Synthesis of N-Substituted a-Amino Acids
4.1 1 Synthesis of a-Amino Acids Carrying Unsaturated
Aliphatic Side-Chains
4.12 Synthesis of a-Amino Acids with Aromatic or
Heteroaromatic Groupings in Side-Chains
4.13 Synthesis of a-(N-Hydroxyarnino) Acids
4.14 Synthesis of a-Amino Acids Carrying
a-(a-Aminoalkyl) Groups, and Related
Nitrogen Functional Groups, in Side-Chains
Contents
4.15 Synthesis of a-Amino Acids Carrying Sulfur- or
Selenium-Containing Side-Chains 35
4.16 Synthesis of a-Amino Acids Carrying Phosphorus
Functional Groups in Side-Chains, and a-Amino
Phosphonic Acids 35
4.17 Synthesis of a-Amino Acids Carrying Boron
Functional Groups in Side-Chains, and
a-Amino Boronic Acids 37
4.18 Synthesis of a-Amino Acids with Silicon
Functional Groups in Side-Chains 37
4.19 Synthesis of Isotopically Labelled a-Amino Acids 37
4.20 Synthesis of P-Amino Acids and Higher
Homologous Amino Acids 39
4.21 Resolution of DL-AminoA cids 46
5 Physico-Chemical Studies of Amino Acids
5.1 X-Ray Crystal Analysis of Amino Acids and
Their Derivatives
5.2 Nuclear Magnetic Resonance Spectroscopy
5.3 Optical Rotatory Dispersion and Circular
Dichroism
5.4 Mass Spectrometry
5.5 Other Spectroscopic Studies of Amino Acids
5.6 Physico-Chemical Studies of Amino Acids
5.7 Molecular Orbital Calculations for Amino Acids
6 Chemical Studies of Amino Acids 58
6.1 Racernization 5 8
6.2 General Reactions of Amino Acids 59
6.3 Specific Reactions of Amino Acids 6 5
6.4 Effects of Electromagnetic Radiation on Amino
Acids 73
7 Analytical Methods
7.1 Introduction
7.2 Gas-Liquid Chromatography
7.3 Ion-Exchange Chromatography
7.4 Thin-Layer Chromatography
7.5 High Performance Liquid Chromatography
7.6 Fluorimetric Analysis
7.7 Capillary Zone Electrophoresis, and Other
Analytical Methods
7.8 Assays for Specific Amino Acids
References 80
Contents
Chapter 2 Peptide Synthesis
By Don T. Elmore
1 Introduction
2 Methods
2.1 Amino-group Protection
2.2 Carboxyl-group Protection
2.3 Side-chain Protection
2.4 Disulfide Bond Formation
2.5 Peptide Bond Formation
2.6 Solid-phase Peptide Synthesis
2.7 Enzyme-mediated Synthesis and Semi-synthesis
2.8 Miscellaneous Reactions Related to Peptide
Synthesis
3 Appendix: A List of Syntheses Reported in 1995
3.1 Natural Peptides, Proteins, and Partial Sequences
3.2 Sequential Oligo- and Poly-peptides
3.3 Enzyme Substrates and Inhibitors
3.4 Conformation of Synthetic Peptides
3.5 Glycopeptides
3.6 Phosphopeptides and Related Compounds
3.7 Immunogenic Peptides
3.8 Nucleopeptides
3.9 Miscellaneous Peptides
3.10 Purification Methods
References
Chapter 3 Analogue and Conformational Studies on Peptide
Hormones and Other Biologically Active Peptides
By S. C.G . Biagini, M. North and P.J. Williams
1 Introduction
2 Peptide-backbone Modifications
2.1 vWHCO]-Retro-inverso Analogues
2.2 v[CH2NH]-Aminomethylenea nd y[CH20]-Ether
Analogues
2.3 v[CH=CH] Isosteres and Related Analogues
2.4 Phosphorus Containing Peptide Bond Isosteres
2.5 Sulfur Containing Peptide Bond Isosteres
2.6 Aldehyde and Ketone Containing Isosteres
2.7 a,a-Dialkylated Glycine Analogues
2.8 Dehydroamino Acid Analogues
2.9 Miscellaneous
Contents
3 Conformationally Restricted Cyclic and Bridged
Analogues
3.1 Rings and Bridges Formed via Arnide Bonds
3.2 Bridges Formed by Disulfide Bonds
3.3 Helices and Helix Inducers
3.4 P-Turn Mimetics and Miscellaneous Bridges
4 Amino Acids with Modified Side-chains, including
Sidechain to Backbone Cyclisations
5 Enzyme Inhibitors
5.1 Renin Inhibitors
5.2 HIV-1 Protease Inhibitors
5.3 Inhibitors of Other Protease Enzymes
5.3.1 Serine Protease Inhibitors
5.3.2 Cysteine Protease Inhibitors
5.3.3 Metalloprotease Inhibitors
5.4 RGD Containing Peptides
5.5 Miscellaneous Enzyme Inhibitors
6 Side Chain Interactions Studied by Residue Substitution
or Deletion and Similar Modifications
6.1 Peptides with Opioid Characteristics
6.2 Neuropeptide Analogues
6.3 Angiotensin Analogues
6.4 Oxytocin and Vasopressin Analogues
6.5 Thrombin Binding Peptides
6.6 Tachykinin Analogues
6.7 Somatostatin Analogues
6.8 Bradikinin Analogues
6.9 Miscellaneous Examples
References
Chapter 4 Cyclic, Modified and Conjugated Peptides
By J. S. Davies
1 Introduction
2 Cyclic Peptides
2.1 General Considerations
2.2 Dioxopiperazines (Cyclic Dipeptides)
2.3 Cyclotripeptides
2.4 Cyclotetrapeptides
2.5 Cyclopentapeptides
2.6 Cyclohexapeptides
Contents
2.7 Cycloheptapeptides
2.8 Cyclooctapeptides
2.9 Cyclononapeptides and Cyclodecapeptides
2.10 Cyclododeca- and Cyclotetradecapeptides
2.1 1 Higher Cyclic Peptides
2.12 Peptides Containing Thiazole/Oxazole Rings
2.13 Cyclodepsipeptides
Modified and Conjugated Peptides
3.1 Phosphopeptides
3.2 Glycopeptide Antibiotics
3.3 Glycopeptides
3.4 Lipopeptides
3.5 Miscellaneous Conjugates
Miscellaneous Structures
References
Chapter 5 p-Lactam Chemistry
By Jan E. Thirkettle, Christopher J. Schofield and
Magnus W. Walter
Introduction
New Natural Products
Biosynthesis
3.1 Penicillin and Cephalosporin Biosynthesis
3.1.1 Early Stages
3.1.2 ACV Synthetase and Related Enzymes
3.1.3 Isopenicillin N Synthase
3.1.4 Cephalosporin Biosynthesis
3.1.5 Penicillin Acylases
3.1.6 Cephalosporin Acylases/Acyltransferases
3.2 Clavam Biosynthesis
3.3 Carbapenem Biosynthesis
3.4 Regulatory and Related Studies
Penicillins and Cephalosporins
Carbacephems
Penems
Carbapenems, Carbapenams, Carbacephems and
Related Systems