Amino Acid Derivatives

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Amino acids are increasingly becoming the first compound that chemists turn to when planning a synthesis leading to a homochiral target. Much of this activity is centered around peptide synthesis, however there is a very wide and demanding range of chemistry that describes the synthesis of derivatives of the *a-amino acids and some uses of those derivatives that do not involve peptides. This book supports several of these areas of chemistry and describes representative methods for introducing substituents at the amino group, modifying carboxy groups, and modifying the side-chains of some common *a-amino acids. There is little discussion of peptide synthesis, although some of the basic protocols in the book are relevant to the modification of amino acids for this purpose. Instead, the authors here focus on the rapidly growing applications of amino acids in many other areas of modern organic synthesis. Any synthetic work carried out by those in the fields of organic and medicinal chemistry will be supported by the detailed practical protocols and background information provided in this book.

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Editorial Reviews

From the Publisher
"This is a compilation of laboratory procedures for transforming amino acids, each procedure with appropriate background, literature references and safety guidance. It covers modification of the amino and carboxyl groups, and numerous and varied modification to the side-chains. The emphasis of this useful book is directed to the use of amino acids in synthesis of peptide analogues and other chiral products, though it also has obvious relevance to peptide synthesis itself."—Aslib Book Guide
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Product Details

  • ISBN-13: 9780198558538
  • Publisher: Oxford University Press, USA
  • Publication date: 1/28/2002
  • Series: Practical Approach in Chemistry Series
  • Pages: 288
  • Product dimensions: 6.30 (w) x 9.30 (h) x 0.80 (d)

Table of Contents

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

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