E-Book Overview
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.
E-Book Content
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 Information Services ISBN 0-85 186-214-4 ISSN 0269-7521 @ The Royal Society of Chemistry. 1992 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 information storage and retrieval systems - without written permission from 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 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 Contents Chapter 1 Amino Acids By G C Barrett 1 Introduction 1 2 Textbooks and Reviews 1 3 Naturally Occurring Amino Acids Isolation of Amino Acids from Natural Sources New Natural Amino Acids New Amino Acids from Hydrolyzates 2 4 Chemical Synthesis and Resolution of Amino Acids General Methods for the Synthesis of a-Amino Acids Asymmetric Synthesig of a-Amino Acids Synthesis of Protein Amino Acids and Other Naturally Occurring a-Amino Acids a-Alkyl and Aryl Analogues of Protein Amino Acids a-Amino Acids Carrying Alkyl Side-Chains, and Cyclic Analogues Prebiotic Synthesis of Amino Acids a -Alkoxy a-Amino Acids Halogeno-alkyl a-Amino Acids a-(U-Hydroxyalkyl) a-Amino Acids a-Amino Acids Carrying Unsaturated Side-chains Aromatic and Heteroaromatic a-Amino Acids N-Substituted a-Amino Acids a-Amino acids containing Sulphur, Selenium, or Tellurium Phosphorus-Containing a-Amino Acids Labelled Amino Acids p- And Higher Amino Acids Resolution of DL-Amino Acids 5 Physico-chemical Studies of Amino Acids Crystal Structures of Amino Acids and Their Derivatives Nuclear Magnetic Resonance Spectrometry Optical Rotatory Dispersion and Circular Dichroism Mass Spectrometry Other Physico-chemical Studies Molecular Orbital Calculations 2 3 3 5 5 10 17 22 23 25 26 26 27 27 29 30 30 30 33 41 46 46 46 48 48 48 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 L