Tags

Type your tag names separated by a space and hit enter

Enantioselectivity of hydroxylation of racemic piperitone by fungi.
Chirality. 2010 Nov; 22(10):929-35.C

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+Show Affiliations

Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20872669

Citation

Grudniewska, Aleksandra, et al. "Enantioselectivity of Hydroxylation of Racemic Piperitone By Fungi." Chirality, vol. 22, no. 10, 2010, pp. 929-35.
Grudniewska A, Gniłka R, Wawrzeńczyk C. Enantioselectivity of hydroxylation of racemic piperitone by fungi. Chirality. 2010;22(10):929-35.
Grudniewska, A., Gniłka, R., & Wawrzeńczyk, C. (2010). Enantioselectivity of hydroxylation of racemic piperitone by fungi. Chirality, 22(10), 929-35. https://doi.org/10.1002/chir.20862
Grudniewska A, Gniłka R, Wawrzeńczyk C. Enantioselectivity of Hydroxylation of Racemic Piperitone By Fungi. Chirality. 2010;22(10):929-35. PubMed PMID: 20872669.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselectivity of hydroxylation of racemic piperitone by fungi. AU - Grudniewska,Aleksandra, AU - Gniłka,Radosław, AU - Wawrzeńczyk,Czesław, PY - 2010/9/28/entrez PY - 2010/9/28/pubmed PY - 2011/1/14/medline SP - 929 EP - 35 JF - Chirality JO - Chirality VL - 22 IS - 10 N2 - 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). SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/20872669/Enantioselectivity_of_hydroxylation_of_racemic_piperitone_by_fungi_ L2 - https://doi.org/10.1002/chir.20862 DB - PRIME DP - Unbound Medicine ER -