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Specialist Periodical Reports provide systematic and detailed review coverage of progress in the major areas of chemical research. Written by experts in their specialist fields the series creates a unique service for the active research chemist, supplying regular critical in-depth accounts of progress in particular areas of chemistry.
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Amino Acids and Peptides Volume 20 A Specialist Periodical Report Amino Acids and Peptides Volume 20 A Review of the Literature Published during 1987 Senior Reporter J. H. Jones, University of Oxford Reporters G. C. Barrett, Oxford Polytechnic J. S. Davies, University College of Swansea I. M. Eggleston, University of Oxford D. T. Elmore, Queen’s University Belfast and University of Oxford P. M. Hardy, University of Exeter R. W. Hay, University of Stirling K. 6. Nolan, University of Surrey A. V. Stachulski, Beecham Pharmaceuticals ISBN 0-85 186-184-9 ISBN 0269-7521 @ The Royal Society of Chemistry, 1989 All Rights Reserved N o part o f this book m a y be reproduced or transmitted in any f o r m or by any means -graphic, electronic, including photocopying, recording taping, or information storage and retrieval systems - without written permission from the Royal Society of Chemistry Published by the Royal Society of Chemistry Burlington House, Piccadilly, London W1 V OBN Printed in England by Whitstable Litho Printers Ltd., Whitstable, Kent Preface Our work this year has been overshadowed by the loss of Ian Galpin. After a peptide apprenticeship at Exeter, he extended his experience as an ICI Postdoctoral Fellow with the late Professor George Kenner at Liverpool. He joined the academic staff there in 1974, and it was his professional base for the rest of his life. A still rising but already leading figure in UK peptide chemistry, he had contributed the chapter on peptide synthesis to every volume of these specialist reports since the eleventh, and would have done so again for the twentieth. He had also recently been elected Secretary-Treasurer of the Peptide and Protein Group of the Royal Society of Chemistry and Biochemical Society. He will therefore be greatly missed, not only in his own country but also abroad. Many of o u r readers will have met him at European or American Peptide Symposia, and will remember him as a convivial conference companion as well as an outstanding peptide chemist. He listed hill-walking as one of his main relaxations: he met his death as the result of sudden bad weather on an expedition in Wales with a colleague on 8 February 1988, aged only 41. B a l l i o l College, Oxford John Jones Contents Amino Acids Bu G. C. Barrett 1 1 Introduction 1 2 Textbooks and Reviews 1 3 Naturally Occurring Amino Acids Occurrence of Known Amino Acids New Natural Amino Acids New Amino Acids from Hydrolysates 4 Chemical Synthesis and Resolution of Amino Acids General Methods Asymmetric Synthesis Synthesis of Protein Amino Acids and Other Naturally Occurring Amino Acids a-Alkyl Analogues of Protein Amino Acids Models for Prebiotic Synthesis of Amino Acids Aliphatic Amino Acids Alkoxy a-Amino Acids Halogenoalkyl Amino Acids Hydroxyalkyl Amino Acids a-Amino Acids with Unsaturated Side Chains a-Amino Acids with Aromatic and Heteroaromatic Side-chain Groups N-Substituted a-Amino Acids a-Amino Acids Containing Sulphur or Selenium Phosphorus-containing a-Amino Acids a-Amino Acids Synthesized for the First Time Labelled Amino Acids Synthesis of P-Amino Acids and Higher Homologous Amino Acids Resolution of Amino Acids Chapter 1 5 6 5 5 7 11 17 17 18 18 18 20 20 21 21 22 22 23 23 26 32 Physical and Stereochemical Studies of Amino Acids Crystal Structures Nucle