Details

Autor(en) / Beteiligte

• Jansen, Rolf
• Irschik, Herbert
• Huch, Volker
• Schummer, Dietmar
• Steinmetz, Heinrich
• Bock, Martin
• Schmidt, Thomas
• Kirschning, Andreas
• Müller, Rolf

Titel

Carolacton - A Macrolide Ketocarbonic Acid that Reduces Biofilm Formation by the Caries- and Endocarditis-Associated Bacterium Streptococcus mutans

Ist Teil von

• European Journal of Organic Chemistry, 2010-03, Vol.2010 (7), p.1284-1289

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2010

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. Targeting Biofilms: The structure elucidation of carolacton – the first highly potent compound from myxobacteria that severely reduces the number of viable cells in biofilms – was achieved by a combination of NMR analyses, chemical derivatization, molecular modeling, and X‐ray analysis, which allowed confirmation of the absolute configuration of all the stereogenic centers.