Molecules 2013, 18(11), 13812-13822; doi:10.3390/molecules181113812
Article

Baeyer-Villiger Oxidation of Some C19 Steroids by Penicillium lanosocoeruleum

Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, Wroclaw 50-375, Poland
Received: 8 September 2013; in revised form: 28 October 2013 / Accepted: 30 October 2013 / Published: 7 November 2013
(This article belongs to the Special Issue Biosynthesis and Biotransformation)
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Abstract: The biotransformation of androsterone (1), epiandrosterone (2), androstanedione (3) and DHEA (dehydroepiandrosterone) (4) by Penicillium lanosocoeruleum—a fungal species not used in biotransformations so far—were described. All the substrates were converted in high yield (70%–99%) into D ring δ-lactones. The oxidation of 1 produced 3α-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (5). The oxidation of 2 led to 3β-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (6). The biotransformation of 3 resulted in the formation of 3α-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (5) and 17a-oxa-D-homo-5α-androstan-3,17-dione (7). An analysis of the transformation progress of the studied substrates as a function of time indicates that the Baeyer-Villiger monooxygenase of this fungus does not accept the 3β-hydroxy-5-ene functionality of steroids. In this microorganism steroidal 3β-hydroxy-dehydrogenase (3β-HSD) was active, and as a result DHEA (4) was transformed exclusively to testololactone (8). Apart from the observed oxidative transformations, a reductive pathway was revealed with the C-3 ketone being reduced to a C-3α-alcohol. It is demonstrated for the first time that the reduction of the 3-keto group of the steroid nucleus can occur in the presence of a ring-D lactone functionality.
Keywords: steroidal lactones; biotransformation; Baeyer-Villiger oxidation; DHEA; androsterone; epiandrosterone; 5α-androstan-3,17-dione; 3β-HSD; Penicillium lanosocoeruleum

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MDPI and ACS Style

Świzdor, A. Baeyer-Villiger Oxidation of Some C19 Steroids by Penicillium lanosocoeruleum. Molecules 2013, 18, 13812-13822.

AMA Style

Świzdor A. Baeyer-Villiger Oxidation of Some C19 Steroids by Penicillium lanosocoeruleum. Molecules. 2013; 18(11):13812-13822.

Chicago/Turabian Style

Świzdor, Alina. 2013. "Baeyer-Villiger Oxidation of Some C19 Steroids by Penicillium lanosocoeruleum." Molecules 18, no. 11: 13812-13822.

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