The first total synthesis of abenquines A, B2, C and D has been achieved in three steps starting from commercially available 2,5-dimethoxyaniline, with overall yields of 41-61%. Four analogues bearing the amino acids d-valine (17), l-methionine (18), and glycine (19), and benzylamine (20), were also prepared in 45-72% yield. The inhibitory properties of these compounds were evaluated against the photoautotrophic growth of a model Synechococcus sp. strain. Abenquine C and its enantiomer were substantially ineffective, whereas all other abenquines significantly inhibited cell proliferation, with concentrations causing 50%-inhibition of algal growth ranging from 10-5 to 10-6 M.

First total synthesis and phytotoxic activity of Streptomyces sp. metabolites abenquines

FORLANI, Giuseppe
2016

Abstract

The first total synthesis of abenquines A, B2, C and D has been achieved in three steps starting from commercially available 2,5-dimethoxyaniline, with overall yields of 41-61%. Four analogues bearing the amino acids d-valine (17), l-methionine (18), and glycine (19), and benzylamine (20), were also prepared in 45-72% yield. The inhibitory properties of these compounds were evaluated against the photoautotrophic growth of a model Synechococcus sp. strain. Abenquine C and its enantiomer were substantially ineffective, whereas all other abenquines significantly inhibited cell proliferation, with concentrations causing 50%-inhibition of algal growth ranging from 10-5 to 10-6 M.
2016
Nain Perez, Amalyn; Barbosa, Luiz C. A.; Maltha, Celia R. A.; Forlani, Giuseppe
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/2359094
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