Hydrolytic kinetic resolution of the enantiomers of the structural isomers trans -1-phenylpropene oxide and (2,3-epoxypropyl)benzene by yeast epoxide hydrolase.
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.
Lotter
Jeanette
J
Department of Pharmaceutical Chemistry, North-West University, Private Bag X6001, 2520 Potchefstroom, South Africa. JLotter2@csir.co.z
Botes
Adriana L
AL
Van Dyk
Martha S
MS
Breytenbach
Jaco C
JC
D004789:Enzyme Activation; D004851:Epoxide Hydrolases / Q000737:chemistry / Q000378:metabolism*; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D006868:Hydrolysis; D007536:Isomerism; D007700:Kinetics; D012248:Rhodotorula / Q000145:classification* / Q000201:enzymology*; D012680:Sensitivity and Specificity; D013045:Species Specificity; D013379:Substrate Specificity
C497707:1-phenylpropene oxide; D004852:Epoxy Compounds; D004851:Epoxide Hydrolases; C497708:(2,3-epoxypropyl)benzene