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Reduction of testosterone, androstendione and their derivatives by Aphanocladium album
Author(s) -
DmochowskaGladysz Jadwiga,
Kolek Teresa,
Siewiński Antoni
Publication year - 1989
Publication title -
journal of basic microbiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.58
H-Index - 54
eISSN - 1521-4028
pISSN - 0233-111X
DOI - 10.1002/jobm.3620290102
Subject(s) - chemistry , ketone , double bond , alcohol , conjugated system , group (periodic table) , methyl group , carbonyl group , medicinal chemistry , allyl alcohol , triple bond , stereochemistry , organic chemistry , catalysis , polymer
A strain of Aphanocladium album reduces the C‐3 carbonyl group in testosterone or androstendione to to 3α‐allyl alcohol. In some derivatives of these steroids the same carbonyl group is reduced to allyl alcohol with stereospecificity, depending on whether chlorine at C‐4 or a 17α‐methyl group is present. On the other hand, the presence of C‐4 methyl group, a C‐19 hydroxy group, a C‐17 acetyl one, or a double bond conjugated with the 4‐en‐3‐ ketone system totally inhibits the formation of allyl alcohols at C‐3. At the samé time, the C‐17 carbonyl group in androstendione or in its derivatives is reduced to a respective 17β‐alcohol. In the derivatives with an additional 2‐exomethylene group the double bond at this group is reduced.