New building blocks for peptide and depsipeptide synthesis: hexafluoroacetone protected L-homoisoserine and D,L-homoisocysteine derivatives, Part 3

Efficient syntheses of L-homoisoserine and D,L-homoisocysteine derivatives starting from L-malic and D,L-thiomalic acid using hexafluoroacetone as protecting and activating agent are described. The new compounds are interesting building blocks for the preparation of non-natural peptides and depsipep...

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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 5; pp. 1059 - 1062
Main Authors Radics, G, Pires, R, Koksch, B, El-Kousy, SM, Burger, K
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 27.01.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SUBSTITUTION
DESIGN
HEXAPEPTIDE
peptide modification
SECONDARY STRUCTURES
GABA derivatives
curtius rearrangement
BETA-PEPTIDES
D,L-homoisocysteine
Wolff rearrangement
GAMMA-PEPTIDES
FOLDAMERS
OMEGA-AMINO ACIDS
L-homoisoserine
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Summary:Efficient syntheses of L-homoisoserine and D,L-homoisocysteine derivatives starting from L-malic and D,L-thiomalic acid using hexafluoroacetone as protecting and activating agent are described. The new compounds are interesting building blocks for the preparation of non-natural peptides and depsipeptides as well as for the construction of new GABA derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(02)02712-0