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New 9,10‐Secosteroids from Biotransformations of Hyodeoxycholic Acid with Rhodococcus spp.
Author(s) -
Costa Stefania,
Giovannini Pier Paolo,
Fantin Giancarlo,
Medici Alessandro,
Pedrini Paola
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200330
Subject(s) - chemistry , rhodococcus , stereochemistry , hydroxylation , side chain , intramolecular force , hemiacetal , organic chemistry , enzyme , polymer
The biotransformations of hyodeoxycholic acid with various Rhodococcus spp. are reported. Some strains ( i.e., Rhodococcus zopfii, Rhodococcus ruber , and Rhodococcus aetherivorans ) are able to partially degrade the side chain at C(17) to afford 6 α ‐hydroxy‐3‐oxo‐23,24‐dinor‐5 β ‐cholan‐22‐oic acid ( 2 ; 23%) and 6 α ‐hydroxy‐3‐oxo‐23,24‐dinorchol‐1,4‐dien‐22‐oic acid ( 3 ; 23–30%), together with two new 9,10‐secosteroids 4 and 5 (10–45%), still bearing the partial side chain at C(17) and adopting an intramolecular hemiacetal form. In addition, the 9,10‐secosteroid 5 showed an unprecedented C(4)‐ hydroxylation. The new secosteroids were fully characterized by MS, IR, NMR, and 2D‐NMR analyses.