[Oxidation of 17alpha,20beta- and 17alpha,20alpha-dihydroxysipregn-4-en-ones--side products of biotransformation of progesterone by recombinant microorganisms expressing cytochrome P45017alpha].
Progesterone biotransformation with recombinant yeast Yarrowia lipolytica E129A15 and Saccharomyces cerevisiae GRF18/YEp5117 alpha expressing bovine adrenocortical cytochrome P45017 alpha yielded 17 alpha-hydroxyprogesterone and two diols, 17 alpha, 20 beta- and 17 alpha, 20 alpha-dihydroxypregn-4-en-3-one. The oxidation of mixtures of the three steroids with chromic acid resulted in the cleavage of 17-20 bonds in the diols with the formation of androst-4-ene-3,17-dione. The biotransformation of pregn-4-ene-20 beta-ol-3-one by means of Y. lipolytica E129A15 was accompanied by the following reactions: the primary oxidation of these compounds to progesterone and the subsequent successive reactions of 17 alpha-hydroxylation and 20 alpha- and 20 beta-reduction. The results widen the possibilities for enzymatic and chemical modifications of steroids. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2003, vol. 29, no. 6; see also http://www.maik.ru.
Shkumatov
V M
VM
Research Institute for Physicochemical Problems, Belarussian State University, ul. Leningradskaya 14, Minsk, 220050 Belarus. biopharm@bsu.by
Usova
E V
EV
Radiuk
V G
VG
Kashkan
Zh N
ZhN
Kovganko
N V
NV
Juretzek
T
T
Mauersberger
S
S
D000302:Adrenal Cortex / Q000201:enzymology; D000818:Animals; D001711:Biotransformation; D002417:Cattle; D010084:Oxidation-Reduction; D011278:Pregnanes / Q000737:chemistry*; D011374:Progesterone / Q000493:pharmacokinetics*; D012441:Saccharomyces cerevisiae / Q000235:genetics; D013254:Steroid 17-alpha-Hydroxylase / Q000235:genetics / Q000378:metabolism*; D025062:Yarrowia / Q000235:genetics
D011278:Pregnanes; D011374:Progesterone; D013254:Steroid 17-alpha-Hydroxylase