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Croatica Chemica Acta, Vol. 45 No. 4, 1973.

Original scientific paper

Mechanism of Hydroxylation of Steroids. Hydroxylation of 16a-Methyl-4-pregnene-21-ol-3,20- dione Acetate with Mucor Griseo-Cyanus

U. Valcavi ; Istituto Biochimico Italiano, 20139 Milano, Italia
M. Japelj ; KRKA, Pharmaceutical and Chemical Works, 68000 Novo Mesto, Slovenia, Yugoslavia
S. Tedeschi ; Istituto Biochimico Italiano, 20139 Milano, Italia

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Abstract

Mucor griseo-cyanus, which introduces an hydroxyl group in
the 14-position of several steroids, converts 16a-methyl-4-pregnene-
21-ol-3,20-dione acetate (I) into a monohydrox:yderiva1Jive for which
the structure 16a-methyl-4-pregnene-7a,21-diol-3,20-dione (III) has
been determined. 16a-Methyl-4-pregnene-21-ol-3,20-dione acetate (I) and 16a- methyl-4-pregnene-7a,21-diol-3,20-dione (III) are transformed by Mucor griseo-cyanus, with a long time of incubation, into a dihydroxyderivative for which the structure 16a-methyl-4-pregnene- 7a,12~,21-triol-3,20-dione triacetate (VI) has been determined. The, 16a-methyl group in compound I inhibits the 14n-hydroxylase of Mucor griseo-cyanus by steric hindrance.

Keywords

Hrčak ID:

197011

URI

https://hrcak.srce.hr/197011

Publication date:

15.4.1974.

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