Amino Acid Derivatives: Amino Acid Derivatives

Hardcover | December 16, 1999

EditorGraham C. Barrett

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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, whichinvariably 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 aminoacids 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.

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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 sy...

Dr Graham Campbell Barrett BSc (Lond) PhD (Lond) DPhil (Oxon) C Chem FRSC 10 Harberton Mead Oxford OX3 0DB Tel/fax: 01865 763322 Email GCBRCB@aol.com

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Format:HardcoverDimensions:286 pages, 9.21 × 6.14 × 0.87 inPublished:December 16, 1999Publisher:Oxford University PressLanguage:English

The following ISBNs are associated with this title:

ISBN - 10:0198558538

ISBN - 13:9780198558538

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Table of Contents

Preface1. Graham C. Barrett: Introduction2. Graham C. Barrett: Acylation and alkoxycarbonylation of the amino group3. Graham C. Barrett: Thioacylatin of the amino group of amino acids4. Graham C. Barrett: Mono- and Di-alkylatin of the amino group5. Graham C. Barrett: Reactions at the carboxy group of an amino acid: Amino acid salts6. Graham C.Barrett: Reactions at the carboxy group of an amino acid: Esterification of amino acids7. K.J. Merchant: Carboxy group modifications; synthesis of a homochiral ketone derived from L-tryptophan8. M.G. Moloney: Synthons derived from Aspartic and glutamic acids9. R.J. Polt: Benzophenone schiff bases of a-Amino acid esters as electrophiles. Addition of grignard reagents and alkly-lithiums to produce threo-amino alcohols and aminopolyols10. P. Meffre et al: Synthetic uses of serine, threonine and cysteine11. P. Meffre et al: Synthetic uses of methionine12. G.T. Crisp: Metal-mediated modification of the side-chains of a-amino acids13. A.S. Anslow et al: Diastereocontrolled functionalisation of enantiomerically pure 5-phenyl-1, 4-Oxazin-2-ones by azomethine ylid generation and trapping14. Graham C. Barrett: Reductive modifications of the carboxy-group15. Reactions at the a-Carbon Atom of a-Amino acid derivatives16. Modifications of the Aryl substitutents of a- and beta-aryl a-amino acids17. I.A. O'Neil: Isolation and chromatographic purification of reaction products from amino acidsIndex

Editorial Reviews

'The emphasis of this useful book is directed to the use of amino acids in synthesis of peptide analogues anfd other chiral products, though it also has obvious relevance to peptide synthesis' Aslib