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Rhizopus nigricans produces Ila-hydroxyprogesterone with a unidentified byproduct, which is hardly separated. Results of chromatography, IR and NMR spectroscopy identified the byproduct to be 1la-hydroxy-allopregnane-3,20-dione. R nigricans was found to transform progesterone into a monoform intermediate, 1la-hydroxyprogesterone, from which 11 a-hydroxy-allopregnane-3,20-dione and 60, Ila-dihydroxyprogesterone were formed respectively by 5a-reduction and 6S-hydroxylation.
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