Amino acid derivatives : a practical approach

Bibliographic Information

Amino acid derivatives : a practical approach

edited by Graham C. Barrett

(The practical approach in chemistry series)

Oxford University Press, c1999

  • : hbk

Available at  / 13 libraries

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Note

Includes bibliographical references and index

Description and Table of Contents

Description

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.

Table of Contents

  • Preface
  • 1. Introduction
  • 2. Acylation and alkoxycarbonylation of the amino group
  • 3. Thioacylatin of the amino group of amino acids
  • 4. Mono- and Di-alkylatin of the amino group
  • 5. Reactions at the carboxy group of an amino acid: Amino acid salts
  • 6. Reactions at the carboxy group of an amino acid: Esterification of amino acids
  • 7. Carboxy group modifications
  • synthesis of a homochiral ketone derived from L-tryptophan
  • 8. Synthons derived from Aspartic and glutamic acids
  • 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
  • 10. Synthetic uses of serine, threonine and cysteine
  • 11. Synthetic uses of methionine
  • 12. Metal-mediated modification of the side-chains of a-amino acids
  • 13. Diastereocontrolled functionalisation of enantiomerically pure 5-phenyl-1, 4-Oxazin-2-ones by azomethine ylid generation and trapping
  • 14. Reductive modifications of the carboxy-group
  • 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
  • Index

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