By William Charney, Hershel L. Herzog
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Additional resources for Microbial Transformations of Steroids. A Handbook
This transformation was first seen by Meystre, Vischer, and Wettstein with Peziza sp. on deoxycorticosterone (M-585) and by Fried and associates with Phycomyces blakesleeanus on progesterone (F-285, F-286). The questions of assignment of configuration at the 7-position have been reviewed thoroughly by Tweit, Goldkamp, and Dodson (T-1037). From their analysis of rotational data, together with appropriate chemical information, unambiguous assignments can be made. 7ff-Hydroxy lation. The first microbial hydr oxy lation, reported by Kramli and Horvath (K-474), was that at the 7 ξ-position by Proactinomyces sp.
H. , J. Am. Chem. Soc. 89, 1956 (1967); Sih, C. J . , Tai, H. H. and Tsong, Y. , p. 1957. II. CHEMICAL CLASSIFICATIONS 54 COOH CH 3 CH 2 COOH From these findings Sih has inferred the details of the mode of microbial degradation of the bisnorcholanic acid in the following manner. He reports that this latter sequence does not require oxygen, on which basis he presumably excludes hydroxylation of the bisnorcholanic acid as an alternative path. 0 aldol He has not reached similar conclusions about the degradation of the cholanic acid to the bisnor acid.
52c The organisms reported here to degrade cholesterol are known to be active 1-dehydrogenation species for 3-ketosteroids. CLASSES O F CHEMICAL REACTIONS 55 and Mitsugi (Ap-37). This degradation is effected with the representative 1-dehydrogenating species, Fusarium solani and Corynehacterium simplex. In these instances there a r e both parallels with and differences from the degradation of the cholesterol side chain. The pathway proposed by Kondo and Mitsugi is illustrated as follows. 0>JI Η0ΗΧ.
Microbial Transformations of Steroids. A Handbook by William Charney, Hershel L. Herzog