Total Synthesis and Antimicrobial Activity of Tumescenamide C and Its Derivatives

Tumescenamide C (1) is an antimicrobial compound produced by Streptomyces sp. KUSC_F05 and consists of a cyclic depsipeptide core and a polyketide side chain with branched methyl groups. Here, we report the total synthesis of tumescenamide C and two derivatives, mainly using Fmoc solid-phase peptide...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-03, Vol.85 (6), p.4530-4535
Main Authors: Takahashi, Nobuaki, Kaneko, Kensuke, Kakeya, Hideaki
Format: Article
Language:English
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Summary:Tumescenamide C (1) is an antimicrobial compound produced by Streptomyces sp. KUSC_F05 and consists of a cyclic depsipeptide core and a polyketide side chain with branched methyl groups. Here, we report the total synthesis of tumescenamide C and two derivatives, mainly using Fmoc solid-phase peptide synthesis (SPPS). In addition, a biological evaluation of these compounds revealed the critical partial structure in 1 for antimicrobial activity.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03516