Studies on Baeyer-Villiger oxidation of steroids: DHEA and pregnenolone d-lactonization pathways in Penicillium camemberti AM83
Teresa Kołek , Anna Szpineter , Alina Świzdor
AbstractPenicillium camemberti AM83 strain is able to carry out effective Baeyer-Villiger type oxidation of DHEA, pregnenolone, androstenedione and progesterone to testololactone. Pregnenolone and DHEA underwent oxidation to testololactone via two routes: through 4-en-3-ketones (progesterone and/or androstenedione respectively) or through 3β-hydroxy-17a-oxa-d-homo-androst-5-en-17-one. Analysis of transformation progress of studied substrates as function of time indicates that the 17β-side chain cleavage and oxidation of 17-ketones to d-lactones are catalyzed by two different, substrate-induced, BVMOs. In the presence of a C-21 substrate (pregnenolone or progesterone) induction of the enzyme catalyzing cleavage at 17β-acetyl chain was observed, whereas DHEA and androstenedione induced activity of the BVMO responsible for the ring-D oxidation; 5-en-3β-alcohol was a more effective inducer that the respective 4-en-3-ketone.
|Journal series||Steroids, ISSN 0039-128X, e-ISSN 1878-5867, (A 25 pkt)|
|Publication size in sheets||0.5|
|Keywords in English||Biotransformation; DHEA; Microbial Baeyer-Villiger oxidation; Penicillium camemberti; Pregnenolone; Steroidal lactones|
|ASJC Classification||; ; ; ; ;|
|Publication indicators||= 33; = 30; : 2009 = 1.095; : 2009 = 2.905 (2) - 2009=2.546 (5)|
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