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

Beilstein Journal of Organic Chemistry

Bernhard Westermann¹  Ricardo A. W. Neves Filho¹  Sebastian Stark¹  Ludger A. Wessjohann¹ 

[1] Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany, Tel: [phone], Fax: [phone] (Address for correspondence);

关键词: antibiotic;    anticancer;    Gram negative bacteria;    natural product;    peptide coupling;    peptides;    peptoid;    toxin;    Ugi reaction;   

DOI  :  10.3762/bjoc.8.234

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown