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

Abstract

Kinetic resolution of the enantiomers of trans -1-phenylpropene oxide and (2,3-epoxypropyl)benzene was achieved by yeasts from the genus Rhodotorula. The resolution of trans -1-phenylpropene oxide by Rhodotorula glutinis 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 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 genera in the enantioselective hydrolysis of epoxides from different structural classes.