Many successful syntheses of homochiral organic compounds use an amino acid derivative as a starting point. Such syntheses are not confined to peptides as targets; peptide synthesis strategies have been narrowed down to a few well-defined protocols (and these are not covered in this book). Outside the peptide field, many non-routine syntheses have been established that give the intended products in which the structural features of the starting amino acid are barely recognisable. This book is a laboratory guide that covers the early stages of syntheses under these headings, which invariably call for modifications to the functional groups of readily-available L-amino acids. It will therefore give invaluable guidance to the preparation of amino acid derivatives to be used not only in these broad area of synthesis but also in amino acid analysis. Synthetic work with amino acids carried out by new users and by experienced chemists and other scientists, will be supported by the detailed practical protocols and background information provided in this book.

Preface 1. Introduction, Graham C. Barrett 2. Acylation and alkoxycarbonylation of the amino group, Graham C. Barrett 3. Thioacylatin of the amino group of amino acids, Graham C. Barrett 4. Mono- and Di-alkylatin of the amino group, Graham C. Barrett 5. Reactions at the carboxy group of an amino acid: Amino acid salts, Graham C. Barrett 6. Reactions at the carboxy group of an amino acid: Esterification of amino acids, Graham C.Barrett 7. Carboxy group modifications; synthesis of a homochiral ketone derived from L-tryptophan, K.J. Merchant 8. Synthons derived from Aspartic and glutamic acids, M.G. Moloney 9. Benzophenone schiff bases of a-Amino acid esters as electrophiles. Addition of grignard reagents and alkly-lithiums to produce threo-amino alcohols and aminopolyols, R.J. Polt 10. Synthetic uses of serine, threonine and cysteine, P. Meffre et al 11. Synthetic uses of methionine, P. Meffre et al 12. Metal-mediated modification of the side-chains of a-amino acids, G.T. Crisp 13. Diastereocontrolled functionalisation of enantiomerically pure 5-phenyl-1, 4-Oxazin-2-ones by azomethine ylid generation and trapping, A.S. Anslow et al 14. Reductive modifications of the carboxy-group, Graham C. Barrett 15. Reactions at the a-Carbon Atom of a-Amino acid derivatives 16. Modifications of the Aryl substitutents of a- and beta-aryl a-amino acids 17. Isolation and chromatographic purification of reaction products from amino acids, I.A. O'Neil Index

'It will be of considerable interest and practical value to anyone making-peptides and peptide analogues' European Peptide society Newsletter