Influence of 1-double bond and 11 beta-hydroxy group on stereospecific microbial reductions of 4-en-3-oxo-steroids.
The yeast Rhodotorula glutinis and the anaerobic bacterium Clostridium paraputrificum were used for stereospecific reductions of 4-chloro-11 beta-hydroxy-17 alpha-methyl-testosterone and the corresponding 1-dehydro compound to prepare 5 alpha- and 5 beta-H derivatives, respectively. C. paraputrificum was able to 5 beta-reduce both substances, whereas the 5 alpha-reduction by R. glutinis was inhibited by the structure elements 1-en and 11 beta-OH so that the substrate with both structure elements was not 5 alpha-reduced. The microbial conversion of the four steroids with and without 1-en and 11 beta-OH was compared in semiquantitative experiments. A number of new substances are described, 11 beta-hydroxy and 11-oxo derivatives of 5 alpha- and 5 beta-dihydro-4-chloro-17 alpha-methyltestosterone including some 3-OH compounds and characterized by NMR, mass spectrometric and further data.
D003013:Clostridium / Q000378:metabolism; D005285:Fermentation; D006900:Hydroxylation; D010084:Oxidation-Reduction; D012248:Rhodotorula / Q000378:metabolism; D013237:Stereoisomerism; D013256:Steroids / Q000378:metabolism*; D013379:Substrate Specificity; D013739:Testosterone / Q000031:analogs & derivatives / Q000378:metabolism
D013256:Steroids; C000430:D-4-chloro-17 beta-hydroxy-3-oxo-17 alpha-methylandrosta-1,4-diene; D013739:Testosterone