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Microbial introduction of a 16α‐hydroxyl function into the steriod nucleus
Author(s) -
Iida M.,
Shinozuka T.,
Iizuka H.
Publication year - 1979
Publication title -
zeitschrift für allgemeine mikrobiologie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.58
H-Index - 54
eISSN - 1521-4028
pISSN - 0044-2208
DOI - 10.1002/jobm.19790190806
Subject(s) - dehydroepiandrosterone , pregnenolone , estrone , hydroxylation , steroid , chemistry , endocrinology , medicine , biochemistry , enzyme , biology , hormone , androgen
The introduction of a 16α‐hydroxyl function into the steroid nucleus was studied in resting cells of Streptomyces roseochromogenes NRRL B‐1233. The oxidation product of dehydroepiandrosterone (DHEA) was identified as 16α‐hydroxy DHEA by suing thin‐layer and gas‐liquid chromatography. A linear relation between cell concentration and 16α‐OH‐DHEA formation was observed. 16α‐Hydroxylase showed good activity at pH 8.0 for 16α‐OH‐DHEA formation. The enzyme showed good activity at 3.1 × 10 −4 M DHEA. The oxidation products of pregnenolone, 4‐androstene‐3,17‐dione, estrone, and 5‐androstene‐3β, 17β–diol as well as of other substrates were identified as the 16α‐hydroxy steroid, respectively. The rates of microbial 16α‐hydroxylation were as follows: 76.9% for DHEA, 50.4% for pregnenolone, 43.9% for 4‐androstene‐3,17‐dione, 34.3% for estrone, and 19.6% for 5‐androstene‐3β, 17β‐diol. The organism tested catalyzes 16α‐hydroxylation of a wide variety of steroids.