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Enantioselectivity of hydroxylation of racemic piperitone by fungi
Author(s) -
Grudniewska Aleksandra,
Gniłka Radosław,
Wawrzeńczyk Czesław
Publication year - 2010
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20862
Subject(s) - chemistry , hydroxylation , organic chemistry , stereochemistry , enzyme
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 ), (+)‐(4 S ,6 R )‐ trans ‐6‐hydroxypiperitone ((+)‐ 3 ), and (+)‐(4 R ,6 R )‐ cis ‐6‐hydroxypiperitone ((+)‐ 4 ). The transformation of this substrate ((±)‐ 1 ) by A. coerulea AM93 gave (±)‐7‐hydroxypiperitone ((±)‐ 2 ), (−)‐(4 R ,6 S )‐ trans ‐6‐hydroxypiperitone (−)‐ 3 ), and (−)‐(4 S ,6 S )‐ cis ‐6‐hydroxypiperitone ((−)‐ 4 ). The last strain studied, A. glauca AM177, converted racemic piperitone ((±)‐ 1 ) to four products: (+)‐( S )‐7‐hydroxypiperitone ( 2 ), (+)‐(4 S ,6 R )‐ trans ‐6‐hydroxypiperitone ((+)‐ 3 ), (±)‐ cis ‐6‐hydroxypiperitone ((±)‐ 4 ), and 8‐hydroxypiperitone ( 5 ). Chirality, 2010. © 2010 Wiley‐Liss, Inc.