Issue 5, 2019

Synthesis and biological activity of dehydrophos derivatives

Abstract

The synthesis of dehydrophos derivatives featuring modified peptide chains, characterized by the presence of substituents in the vinyl moiety, or possessing a phosphonic acid monoalkyl ester other than the monomethyl ester one, has been accomplished by a versatile procedure based on Horner–Wadsworth–Emmons olefination with suitable aldehydes and on the selective hydrolysis of the dialkyl phosphonate group. Such derivatives have been tested against a series of bacterial strains, using the naturally occurring peptide, dehydrophos, for comparison. Thus, the effects of the aforementioned structural variations on antimicrobial activity have been studied.

Graphical abstract: Synthesis and biological activity of dehydrophos derivatives

Supplementary files

Article information

Article type
Paper
Submitted
11 Dec 2018
Accepted
02 Jan 2019
First published
02 Jan 2019

Org. Biomol. Chem., 2019,17, 1097-1112

Synthesis and biological activity of dehydrophos derivatives

M. M. Jiménez-Andreu, A. Lucía Quintana, J. A. Aínsa, F. J. Sayago and C. Cativiela, Org. Biomol. Chem., 2019, 17, 1097 DOI: 10.1039/C8OB03079K

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