Backbone-modified oligopeptidic bioregulators. The synthesis and configuration of thioamide, amidoxime, cyanoamidine, and amidrazone analogs of the chemotactic peptide N-formyl-methionyl-leucyl-phenylalanine (f-Met-Leu-Phe-OR)

Reaction conditions for the synthesis of thioamide, amidoxime, and N-substituted amidine analogs of the peptide bond are described. Several new amidine analogs of the chemotactic peptide f-Met-Leu-Phe-OR were synthesized using the thioamides as precursors. The assignment of the E/Z configuration was...

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Bibliographic Details
Published in:Canadian journal of chemistry 1985-11, Vol.63 (11), p.3089-3101
Main Authors: Sauvé, Gilles, Rao, Vanga S, Lajoie, Gilles, Belleau, Bernard
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
N-formyl-methionyl-leucyl-phenylalanine
Organic chemistry
peptide synthesis
Peptides
Preparations and properties
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Description
Summary:Reaction conditions for the synthesis of thioamide, amidoxime, and N-substituted amidine analogs of the peptide bond are described. Several new amidine analogs of the chemotactic peptide f-Met-Leu-Phe-OR were synthesized using the thioamides as precursors. The assignment of the E/Z configuration was accomplished by nuclear magnetic resonance. The biological activity of these analogs is briefly described.
ISSN:0008-4042
1480-3291
DOI:10.1139/v85-511