Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC)) vol. 22 PDF
Preview Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC)) vol. 22
A Specialist Periodical Report Amino Acids and Peptides Volume 22 A Review of the Literature Published during 1989 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 P. M. Hardy, University of Exeter R. W. Hay, University of St Andrews K. B. Nolan, The Royal College of Surgeons in Ireland C. H. Frydrych, Beecham Pharmaceuticals ISBN 0-85 186-204-7 ISSN 0269-7521 @ The Royal Society of Chemistry, 1991 All Rights Reserved No part of this book may be reproduced or transmitted in any form of by any means - graphic, electronic, including photocopying, recording, taping, or information storage and retrieval systems - without written permission fiom the Royal Society of Chemistry Published by the Royal Society of Chemistry Thomas Graham House, Cambridge CB4 4WF Printed and bound in England by Bookcraft (Bath) Ltd. Preface During the year under review, peptide science continued its relentless growth. Output still increases, beyond, it seems, control. What might loosely be called straight peptide chemistry has more than five thousand workers engaged in it full-time, producing around a thousand publications a year and flocking to international meetings in their hundreds. Furthermore, what is published on some topics is, as we all know, less complete (and sometimes, one suspects, less interesting) than that which is not, because commercial considerations impose paranoid secrecy. With the subject now so extensive, and'its aficionados so numerous, the emergence of specialised societies was inevitable. Many countries have had semi-formal peptide discussion groups for some time (the UK Peptide and Protein Group was initiated under the auspices of the Chemical and Biochemical Societies as long ago as 1968), and an informal European Peptide Committee has been organising symposia for over thirty years. This movement has now gone a stage further with the formation of, and approval of governing statutes for, a European Peptide Society, in 1989; this was followed by similar formalitites for the birth of an American Peptide Society and a Japanese Peptide Society, both early in 1990. In only a few months the enrolment of the European Peptide Society had risen to over seven hundred, powerful evidence of the field's strength. Balliol College. Oxford John Jones Cont ents Chapter 1 Amino Acids By G C Barrett 1 Introduction 2 Textbooks and Reviews 3 Naturally Occurring Amino Acids Isolation of Amino Acids from Natural Sources Occurrence of Known Amino Acids New Natural Amino Acids New Amino Acids from Hydrolyzates 4 Chemical Synthesis and Resolution General Methods for the Synthesis of a-Amino Acids Asymmetric Synthesis of a-Amino Acids Synthesis of Protein Amino Acids and Other Naturally Occurring a-Amino Acids a-Alkyl Analogues of Protein Amino Acids Alicyclic a-Amino Acids and Close Relatives Models for Prebiotic Synthesis of Amino Acids a-Alkoxy a-Amino Acids Halogenoalkyl a-Amino Acids Hydroxyalkyl a-Amino Acids a-Amino Acids with Unsaturated Side-chains a-Amino Acids with Aromatic and Heteroaromatic Side-chains N-Substituted a-Amino Acids a-Amino Acids Containing Phosphorus Functional Groups Labelled Amino Acids p- and Higher Amino Acids Resolution of a-Amino Acids 5 Physical Studies of Amino Acids Crystal Structures Nuclear Magnetic Resonance Spectrometry Optical Rotatory Dispersion and Circular Dichroism Mass Spectrometry Other Physical Studies Molecular Orbital Calculations Amino Acids and Peptides 6 Chemical Studies of Amino Acids Racemization General Reactions of Amino Acids Specific Reactions of Amino Acids Effects of Electromagnetic Radiation on Amino Acids 7 Analytical Methods General Gas-liquid Chromatography Ion-exchange Chromatography Thin Layer Chromatography High Performance Liquid Chromatography Fluorescence Analysis Other Analytical Methods Determination of Specific Amino Acids References Chapter 2 Peptide Synthesis By D T Elmore 1 Introduction 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 Miscellaneous Reactions Related to Peptide Synthesis 3 Selected Examples of Peptide Synthesis 4 Appendix. A List of Syntheses Reported in 1989 Natural Peptides, Proteins, and and Partial Sequences Sequential Oligo- and Poly-peptides Enzyme Substrates and Inhibitors Conformation of Synthetic Peptides Glycopeptides Phosphopeptides and Related Compounds Immunogenic Peptides Miscellaneous Peptides 5 Purification Methods References Contents Chapter 3 Analogue and Conformational Studies on Peptide Hormones and Other Biologically Active Peptides 145 By J S Davies 1 Introduction 145 2 Peptide-backbone Modifications y[CSNH]-Analogues (and retro-inverso version) y[NCHO]-Retro-Inverso Analogues y[CH2NH]-Amino Methylene Analogues (and retro-Forms) Y[CH=CH]-Ethylenic Isosteres y[COCH2]-Ketomethylene Surrogates Phosphono-Peptides y[S02NH]-Sulphonamide Isosteres y[CN 1-Tetrazole Surrogates y [CHfAlkyl )NH]- Surrogates y[CON(Me)]-N-Methylated Analogues Replacement of L- by D-Residues y[COO]-Depsipeptides Hydrazinopeptides Aza-Peptides C-Terminal Modifications a,a-Dialkylated Glycine Analogues 3 Conformationally Restricted Cyclic and Bridged Analogues 157 Rings and Bridges formed via Amide Bonds 157 Bridges formed by Disulfide Bonds 159 Miscellaneous Bridges and @-Turn Mimetics 161 4 Dehydroamino Acid Analogues 161 5 Enzyme Inhibitors 163 Angiotensin Converting Enzyme (ACE) Inhibitors 163 Renin Inhibitors 165 Inhibitors of Other Enzymes 169 6 Side-Chain Interactions Studied by Residue Substitution or Deletion and Similar Modifications 171 Peptides with Opioid Characteristics 171 Cholecystokinin Analogues 176 Angiotensin and Analogues 177 Vasopressin Analogues 179 0-Phosphorylated and Glycosylated Derivatives 181 Miscellaneous Examples 182 Amino Acids and Peptides 7 Conformational Information derived from Physical Methods Nuclear Magnetic Resonance and Related Techniques X-Ray Crystallography Circular Dichroism/Theoretical and Computational Methods References Chapter 4 Cyclic, Modified, and Conjugated Peptides By P M Hardy 1 Introduction 2 Cyclic Peptides Naturally Occurring Dioxopiperazines (Cyclic Dipeptides) Other Dioxopiperazines Cyclic Tripeptides Cyclic Tetrapeptides Cyclic Pentapeptides Cyclic Hexapeptides Cyclic Hepta- and Octapeptides Higher Cyclic Peptides Cyclodepsipeptides Cyclic Peptides Containing Thiazole and Oxazoline Rings Cyclic Peptides Containing Other Non-protein Ring Components 3 Modified Linear Peptides Enzyme Inhibitors Dehydropeptides Peptides containing a,a-Dialkylamino Acids Amide-Bond Analogues Y-Glutamyl Peptides Conformationally Constrained Peptides Phosphonopeptides Peptides Containing Modified Protein Constituents Peptides Containing Other Unusual Amino Acids 4 Conjugate Peptides Glycopeptide Antibiotics Other Glycopeptides Non-Carbohydrate Peptide Conjugates References Chapter 5 $-Lactan Antibiotic Chemistry By C H Frydrych 1 Introduction 2 New Natural Products Contents 3 Biosynthesis 294 4 Penicillins and Cephalosporins 297 5 Clavulanic Acid and Oxapenams 306 6 Penems 306 7 Carbapenems, Carbacephems, and Related Systems 8 Azetidinones 312 Reactions in Which One Bond is Formed 312 1-2 Bond-forming Reactions 312 3-4 Bond-forming Reactions 313 1-4 Bond Forming Reactions 314 Reactions in Which Two Bonds are Formed 316 - [3+1] Additions: 1-2 and 2-3 Bond Formation 316 - [2+2] Additions 316 1-2 and 2-3 Bond Formation 316 1-2 and 3-4 Bond Formation 319 Chemistry of Azetidinones 319 Further Uses of Azetidinones 323 9 Major Structural Variants 323 10 Mechanistic Studies, Mode of Action, and Degradation Appendix: p-Lactam Antibiotics Prepared for Structure-activity Relationships and Miscellaneous p-Lactams 332 References 334 Chapter 6 Metal Complexes of Amino Acids and Peptides 343 By R W Hay and K B Nolan 1 Introduction 343 2 Amino Acid Complexes 343 Synthesis and Crystal Structures 343 Equilibrium Studies 349 Reactions in Solution 353 3 Peptide Complexes 354 Crystal Structures, Synthesis 355 Stability Constants, Species in Solution 359 Reactions in Solution 365 Miscellaneous 368 References 369 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.
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