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The multicomponent approach to N-methyl peptides: total synthesis of antibacterial (-)-viridic acid and analogues.

ABSTRACT: Two syntheses of natural viridic acid, an unusual triply N-methylated peptide with two anthranilate units, are presented. The first one is based on peptide-coupling strategies and affords the optically active natural product in 20% overall yield over six steps. A more economical approach with only four steps leads to the similarly active racemate by utilizing a Ugi four-component reaction (Ugi-4CR) as the key transformation. A small library of viridic acid analogues is readily available to provide first SAR insight. The biological activities of the natural product and its derivatives against the Gram-negative bacterium Aliivibrio fischeri were evaluated.

SUBMITTER: Neves Filho RA

PROVIDER: S-EPMC3511043 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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The multicomponent approach to N-methyl peptides: total synthesis of antibacterial (-)-viridic acid and analogues.

Neves Filho Ricardo A W RA Stark Sebastian S Westermann Bernhard B Wessjohann Ludger A LA

Beilstein journal of organic chemistry 20121128

Two syntheses of natural viridic acid, an unusual triply N-methylated peptide with two anthranilate units, are presented. The first one is based on peptide-coupling strategies and affords the optically active natural product in 20% overall yield over six steps. A more economical approach with only four steps leads to the similarly active racemate by utilizing a Ugi four-component reaction (Ugi-4CR) as the key transformation. A small library of viridic acid analogues is readily available to provi ...[more]

PMID: 23209543

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