Structure and syntheses of texazone. 2-(N-methylamino)-3H-phenoxazin-3-one-8-carboxylic acid, an actinomycete metabolite.
Cultures of actinomycete strain WRAT-210 produced a dark red crystalline metabolite which was named texazone. Spectroscopic evidence suggested that the structure of texazone is 2-(N-methylamino)-3H-phenoxazin-3-one-8-carboxylic acid. The structure was confirmed by chemical synthesis through oxidative dimerization of ethyl 3-amino-4-hydroxybenzoate with 2-(N-methylamino)phenol and subsequent hydrolysis of the resultant phenoxazinone ester.
D000190:Actinomyces / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010078:Oxazines / Q000096:biosynthesis* / Q000302:isolation & purification; D013053:Spectrophotometry
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D010078:Oxazines; C038757:texazone