Hydrolytic kinetic resolution of the enantiomers of the structural isomers trans -1-phenylpropene oxide and (2,3-epoxypropyl)benzene by yeast epoxide hydrolase

Author: Lotter Jeanette   Botes Adriana L.   van Dyk Martha S.  

Publisher: Springer Publishing Company

ISSN: 0141-5492

Source: Biotechnology Letters, Vol.26, Iss.15, 2004-08, pp. : 1197-1200

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Abstract

Kinetic resolution of the enantiomers of trans</i>-1-phenylpropene oxide and (2,3-epoxypropyl)benzene was achieved by yeasts from the genus Rhodotorula</i>. The resolution of trans</i>-1-phenylpropene oxide by Rhodotorula glutinis</i> UOFS Y-0123 yielded (1R,2R)-epoxide (ee >98%, yield 30%) and (1R,2S)-diol (ee 95%, yield 40%). The highest enantio- and regioselectivity toward (2,3-epoxypropyl)benzene resided in Rhodotorula</i> sp. UOFS Y-0448 (E = 6.16), yielding (S)-epoxide (ee 64%, yield 33%) and (R)-diol (ee 67%, yield 28%). This confirms the superiority of yeasts from the Basidiomycetes</i> genera in the enantioselective hydrolysis of epoxides from different structural classes.