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The ability of Armillariella mellea to transform cyclic monoterpenic alcohols and their acetates
Author(s) -
DraczyńskaŁusiak B.,
Siewiński A.
Publication year - 1991
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.3620310512
Subject(s) - chemistry , hydroxylation , triol , enantiomer , hydrolysis , diol , organic chemistry , menthol , acetylation , transformation (genetics) , stereochemistry , enzyme , biochemistry , gene
An Armillariella mellea culture was found to transform trans ‐ sobrerol to a very small extent, whereas menthol resisted its action altogether. Acetylation of both alcohols, on the other hand, reappointed their reactivity in the same A. mellea culture. Thus, trans‐sobrerol monoacetate and menthyl acetate underwent a two‐step transformation involving hydroxylation (preserving the acetate link) to 3‐acetoxy‐6,8‐ p ‐methen‐diol and 8‐hydroxymenthyl acetate, respectively, which were converted by hydrolysis to 3,6,8‐ p ‐menthen‐triol and 8‐hydroxymenthol, respectively. The transformation of racemic menthyl acetate was enantiospecific; (−) 8‐hydroxymenthol that was formed after 21 days contained 98% of enantiomer 1R, 3R, 4S.