Publication Date:
2013-11-16
Description:
The biotransformations of cholic, deoxycholic, and hyocholic acids with Rhodococcus ruber are reported. In all biotransformations, the C 17 -side chain is partially degraded, and the new 9,10-secosteroids 4a (54%) and 4b (55%) are obtained from cholic and deoxycholic acids, respectively. The loss of H 2 O from C(11) C(12) of secosteroids 4a and 4b affords the compounds 5a (5%) and 5b (20%), respectively. On the other hand, in the biotransformation of hyocholic acid with R. ruber the 9,10-secosteroid 4c is not detected, but, rearranging to an intramolecular hemiacetal form, it evolves to the final furan derivative 6c (35%) by easy elimination of two molecules of H 2 O. The new secosteroids were characterized by IR, NMR, and 2D-NMR spectroscopy, and mass spectroscopy.
Print ISSN:
0018-019X
Electronic ISSN:
1522-2675
Topics:
Chemistry and Pharmacology
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