Microbial hydroxylation of steroids. 7. Hydroxylation of B-nortestosterone and related compounds by Rhizopus arrhizus ATCC 11145, and 13C nuclear magnetic resonance spectra of some B-norsteroids

1981 ◽  
Vol 59 (11) ◽  
pp. 1651-1655 ◽  
Author(s):  
Herbert L. Holland

The incubation of B-norandrost-4-ene-3-ones and B-nor-3β-hydroxyandrost-5-enes with Rhizopus arrhizus ATCC 11145 has been described. The products are consistent with a mechanism of oxidation at C-6 in which the stereochemistry of substitution at C-6 is controlled by stereoelectronic interactions in the substrate, and is not dictated by enzymic constraint during the reaction. The carbon-13 nuclear magnetic resonance spectra of several B-nor-Δ4 and Δ5 steroids have been presented.


1979 ◽  
Vol 57 (23) ◽  
pp. 3069-3072 ◽  
Author(s):  
Herbert L. Holland ◽  
Everton M. Thomas

The 13Cmr spectra of 21-haloprogesterones have been assigned, and chemical shifts compared with those of simple α-haloketones. In addition, the 13Cmr spectra of some C-5α and C-6β halosteroids are presented, and long range 13C—19F coupling observed between C-19 and the C-6β fluorine in some cases. The spectra of several oxygenated analogues and of a series of 5α-hydroxy-6-ketosteroids are also discussed.







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