Influence of substituents at C11 on hydroxylation of progesterone analogs by Bacillus sp.
Transformation of progesterone analogs viz., progesterone, 11 alpha-, 11 beta-hydroxyprogesterones and 11-ketoprogesterone by Bacillus sp. is reported. Both progesterone and 11-ketoprogesterone were hydroxylated while the C(11) epimeric alcohols of progesterone remained unaltered under the conditions used. The major bioconverted products obtained from progesterone and 11-ketoprogesterone were characterized as 6 beta- and 14 alpha-hydroxyprogesterones and 14 alpha-hydroxy-11-ketoprogesterone respectively by mass and NMR spectra. The conversion of 11-ketoprogesterone to its 14 alpha-hydroxy derivative by microbe is unprecedented and novel. Moreover, hydroxylation at 6 beta- and 14 alpha-positions of progesterone by Bacillus sp. is significant. In conclusion, the present data showed that the substituents at 11-position of steroid play important role on hydroxylation by microbe.
Das
Shuvendu
S
Department of Microbiology, Bose Institute, P-1/12 CIT Scheme VII M, 700 054, Kolkata, India
Dutta
Tapan K
TK
Samanta
Timir B
TB
D001407:Bacillus / Q000378:metabolism*; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D011374:Progesterone / Q000031:analogs & derivatives* / Q000378:metabolism*
D011374:Progesterone; C016531:11-ketoprogesterone