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Precursor‐Directed Syntheses and Biological Evaluation of New Elansolid Derivatives
Author(s) -
Steinmetz Heinrich,
Zander Wiebke,
Shushni Muftah A. M.,
Jansen Rolf,
Gerth Klaus,
Dehn Richard,
Dräger Gerald,
Kirschning Andreas,
Müller Rolf
Publication year - 2012
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201200228
Subject(s) - micrococcus luteus , anthranilic acid , fermentation , conjugate , chemistry , staphylococcus aureus , nucleophile , michael reaction , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , bacteria , biology , escherichia coli , catalysis , gene , mathematical analysis , genetics , mathematics
The antibiotic elansolid C1 ( 8 ) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 ( 1* ). This Michael‐type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 ( 9 – 29 ) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus , Micrococcus luteus , and the mouse cell line L929.