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Synthesis of Tetramic Acid Fragments Derived from Vancoresmycin Showing Inhibitory Effects towards S. aureus
Author(s) -
Wingen Lukas Martin,
Rausch Marvin,
Schneider Tanja,
Menche Dirk
Publication year - 2020
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202000241
Subject(s) - moiety , pharmacophore , staphylococcus aureus , escherichia coli , stereochemistry , chemistry , antimicrobial , biosynthesis , inhibitory postsynaptic potential , biochemistry , combinatorial chemistry , bacteria , biology , organic chemistry , enzyme , genetics , neuroscience , gene
An efficient route to various vancoresmycin‐type tetramic acids has been developed. The modular route is based on an effective Fries‐type rearrangement to introduce various appending acetyl residues. The minimum inhibitory concentration (MIC) values of the new tetramic acids against Staphylococcus aureus and Escherichia coli were determined, revealing that three of the new compounds exhibit antimicrobial activity against S. aureus . These bioactive compounds were structurally most closely related to the authentic vancoresmycin building block. Additionally, the compounds induced a lial ‐ lux bioreporter, which responds to cell wall stress induced by antibiotics that interfere with the lipid II biosynthesis cycle. These data suggest the tetramic acid moiety to be a part of the vancoresmycin pharmacophore.