Enantioselectivity of hydroxylation of racemic piperitone by fungi.
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).
Grudniewska
Aleksandra
A
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
Gniłka
Radosław
R
Wawrzeńczyk
Czesław
C
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
D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; C496656:piperitone