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Microbial oxidation of dehydroepiandrosterone and related compounds
Author(s) -
Iida M.,
Matsuhashi K.,
Nakayama T.
Publication year - 1975
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.19750150306
Subject(s) - dehydroepiandrosterone , estrone , chemistry , yield (engineering) , substrate (aquarium) , stereospecificity , steroid , biotransformation , endocrinology , medicine , stereochemistry , biochemistry , enzyme , biology , androgen , hormone , catalysis , ecology , materials science , metallurgy
The oxidation of dehydroepiandrosterone (DHEA), 4‐androstene‐3,17‐dione, and estrone with Streptomyces roseochromogenes NRRL B‐1233 was studied. The oxidation products were isolated and identified as 16α‐hydroxy‐DHEA, 16α‐hydroxy‐4‐androstene‐3,17‐dione and 16α‐hydroxy‐estrone. The yields of these three products were 85%, 41% and 18%, respectively. This indicates the substrate stereospecificity of 16α‐hydroxylase of the organism. An interrelationship between cell growth and the formation of 16α‐hydroxylated steroid was observed in any case. For formation of 16α‐hydroxy‐DHEA, 16α‐hydroxylase showed good activity at DHEA concentration of 3.47 × 10 −4 M. In the case of DHEA, 16α‐hydroxy‐4‐androstene‐3,17‐dione and 5‐androstene‐3β, 16α, 17β‐triol were obtained after the yield of 16α‐hydroxy‐DHEA reached the maximum yield for about 30 hr. The oxidation pathway of DHEA is discussed.