ABSTRACT
Two hundred eighty-five fungi, including 100 basidiomycetes and 35 yeasts, 75 actinomycetes, and 40 bacteria were screened for their ability to convert 5-anilino-1,2,3,4-thiatriazole (AT) to 5-(p-hydroxyanilino)-1,2,3,4-thiatriazole (p-HT). Eleven cultures were found that formed p-HT, which was isolated and whose structure was determined. Aspergillus tamarii NRRL 3280 formed 8.6 g of p-HT/liter from 10 g of AT/liter (78.9% conversion) in shaken flasks and 4.57 g of p-HT/liter from 6 g of AT/liter (69.8% conversion) in 30-liter fermentors. Washed cells of A. tamarii NRRL 3280 also carried out this conversion. 5-(o-hydroxyanilino)-1,2,3,4-thiatriazole (o-HT) was identified as a second product formed by Aspergillus terreus NRRL 1960.
Subject(s)
Aniline Compounds/metabolism , Antihypertensive Agents/biosynthesis , Bacteria/metabolism , Fungi/metabolism , Triazoles/metabolism , Antihypertensive Agents/isolation & purification , Aspergillus/metabolism , Chemical Phenomena , Chemistry , Chromatography, Thin Layer , Culture Media , Fermentation , Hydroxylation , Magnetic Resonance Spectroscopy , Mass Spectrometry , Species Specificity , Spectrophotometry, Infrared , Spectrophotometry, UltravioletSubject(s)
Nitriles/metabolism , Penicillium/metabolism , Pyrrolidines/metabolism , Amides/biosynthesis , Chemical Phenomena , Chemistry , Chromatography , Chromatography, Thin Layer , Deuterium , Infrared Rays , Magnetic Resonance Spectroscopy , Mass Spectrometry , Propionates/metabolism , Pyrimidinones/biosynthesis , Pyrrolidines/biosynthesis , Spectrophotometry , Ultraviolet RaysABSTRACT
Approximately 700 cultures of various types were examined for their ability to hydroxylate acetanilide. The major product formed by unidentified Streptomyces species RJTS-539 was identified as 4'-hydroxyacetanilide (N-acetyl-p-aminophenol). This culture gave a peak yield of 405 mg per liter from 1,000 mg of acetanilide per liter. Considerably lower yields of 4'-hydroxyacetanilide were isolated from S. cinnamoneus NRRLB-1285. The major conversion product of acetanilide formed by Amanita muscaria F-6 was identified as 2'-hydroxyacetanilide, with a peak yield of 433 mg per liter from 1,000 mg per liter of substrate. A small amount of 4'-hydroxyacetanilide was also formed. Six other Streptomyces cultures formed small amounts of one or two products identical or similar to 2'-hydroxyacetanilide or 4'-hydroxyacetanilide as determined by thin-layer chromatography and ultraviolet spectra.
