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Carolacton – A Macrolide Ketocarbonic Acid that Reduces Biofilm Formation by the Caries‐ and Endocarditis‐Associated Bacterium Streptococcus mutans
Author(s) -
Jansen Rolf,
Irschik Herbert,
Huch Volker,
Schummer Dietmar,
Steinmetz Heinrich,
Bock Martin,
Schmidt Thomas,
Kirschning Andreas,
Müller Rolf
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901126
Subject(s) - chemistry , streptococcus mutans , biofilm , microbiology and biotechnology , derivatization , bacteria , streptococcus , dental plaque , antibiotics , endocarditis , biochemistry , chromatography , mass spectrometry , biology , medicine , genetics , surgery
The macrolide ketocarbonic acid carolacton ( 1 ) was isolated from the myxobacterium Sorangium cellulosum , strainSo ce960, because of its antibiotic activity. Subsequently, carolacton ( 1 ) was discovered to be a highly potent agent against biofilms containing the caries‐ and endocarditis‐associated bacterium Streptococcus mutans . The 2D structure of 1 was elucidated by HRMS, IR and 2D NMR spectroscopy. Initially, the stereogenic centres were determined by chemical derivatization in combination with computional methods and finally verified by X‐ray analysis.