Stereospecific sulfur oxidation of 7-methylthioxanthone-2-carboxylic acid by Calonectria decora.
Thin-layer chromatography was used to determine the ability of three microorganisms capable of sulfur oxygenation, including Aspergillus niger, Streptomyces armentosus subsp. armentosus, and Calonectria decora, to oxidize 7-methylthioxanthone-2-carboxylic acid to the corresponding sulfoxide in growing cultures. In addition, optical rotary dispersion, circular dichroism, and nuclear magnetic resonance analysis in the presence of chiral shift reagent were used variously to access reaction stereoselectivity, absolute configuration, and optical purity of isolated products. The data indicated that C. decora produced the sulfoxide in high yield (69%) and optical purity (97%), most probably in the S-configuration.
D001234:Aspergillus niger / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D006999:Hypocreales / Q000378:metabolism*; D008154:Lucanthone / Q000031:analogs & derivatives* / Q000378:metabolism; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013302:Streptomyces / Q000378:metabolism; D013455:Sulfur / Q000378:metabolism*
D013455:Sulfur; D008154:Lucanthone; C015365:7-methylthioxanthone-2-carboxylic acid