THE GAMMA-METHYL-E-OLEFIN AS ISOSTERIC REPLACEMENT OF THE PEPTIDE-BOND

Authors
DEVADDER S VERHEYDEN P JASPERS HCM VANBINST G TOURWE D
Citation
S. Devadder et al., THE GAMMA-METHYL-E-OLEFIN AS ISOSTERIC REPLACEMENT OF THE PEPTIDE-BOND, Tetrahedron letters, 37(5), 1996, pp. 703-706
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
5
Year of publication
1996
Pages
703 - 706
Database
ISI
SICI code
0040-4039(1996)37:5<703:TGAIRO>2.0.ZU;2-1
Abstract
Different olefination methods on Boc-phenylalanine methyl ketone for t he synthesis of gamma-methyl-E-olefin Phe-Gly isosteres are investigat ed. The Horner phosphonate reagent gave the highest yield of E-isomer. The conformational behaviour of four tetrapeptides containing the E-o lefin isostere with and without a vinyl methyl group is studied by H-1 NMR. No evidence for turn structures is found.