title: Enantioselectivity of hydroxylation of racemic piperitone by fungi.
abstract: The biotransformation of racemic piperitone ((±)-1) was investigated using four strains of fungi selected in the screening procedure. The substrate was transformed by Botrytis cinerea AM235, Absidia cylindrospora AM336, Absidia coerulea AM93, and Absidia glauca AM177 into more polar metabolites. The transformation of racemic piperitone ((±)-1) catalyzed by B. cinerea AM235 gave 7-hydroxypiperitone (2) as the only product. The biotransformation of (±)-1 by A. cylindrospora AM336 afforded mixture of three products: (-)-(R)-7-hydroxypiperitone ((-)-2), (+)-(4S,6R)-trans-6-hydroxypiperitone ((+)-3), and (+)-(4R,6R)-cis-6-hydroxypiperitone ((+)-4). The transformation of this substrate ((±)-1) by A. coerulea AM93 gave (±)-7-hydroxypiperitone ((±)-2), (-)-(4R,6S)-trans-6-hydroxypiperitone (-)-3), and (-)-(4S,6S)-cis-6-hydroxypiperitone ((-)-4). The last strain studied, A. glauca AM177, converted racemic piperitone ((±)-1) to four products: (+)-(S)-7-hydroxypiperitone (2), (+)-(4S,6R)-trans-6-hydroxypiperitone ((+)-3), (±)-cis-6-hydroxypiperitone ((±)-4), and 8-hydroxypiperitone (5).
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Grudniewska
authors.forename: Radosław
authors.initials: R
authors.lastname: Gniłka
authors.forename: Czesław
authors.initials: C
authors.lastname: Wawrzeńczyk
mesh_terms: D001711:Biotransformation; D000081005:Cyclohexane Monoterpenes; D005658:Fungi / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D039821:Monoterpenes / Q000737:chemistry / Q000378:metabolism*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
chemical_list: D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; C496656:piperitone