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Enantio‐ and regioselectivity in the epoxide‐hydrolase‐catalyzed ring opening of simple aliphatic oxiranes: Part I: Monoalkylsubstituted oxiranes
Author(s) -
Wistuba D.,
Schurig V.
Publication year - 1992
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.530040309
Subject(s) - chemistry , regioselectivity , epoxide , epoxide hydrolase , hydrolysis , nucleophile , enantiomer , substrate (aquarium) , diol , ring (chemistry) , stereochemistry , catalysis , microsomal epoxide hydrolase , organic chemistry , enzyme , microsome , oceanography , geology
The in vitro conversion of chiral aliphatic monoalkylsubstituted oxiranes into 1,2‐diols catalyzed by epoxide hydrolase of rat liver microsomes occurs with substrate enantioselectivity and regioselectivity. Substrate enantioselectivity is generally low, and has the same sense, for methyloxirane, vinyloxirane, epichloro‐, and epibromohydrin. In the hydrolysis of t ‐butyloxirane inhibitory effects are involved leading to a complex pattern of enantioselectivity . All investigated monosubstituted aliphatic oxiranes are hydrolyzed with high regioselectivity by nucleophilic attack of water at the unsubstituted ring carbon atom. The enantiomeric excess of the unreacted oxirane substrates and the diol metabolites formed were determined by complexation and inclusion gas chromatography. © 1992 Wiley‐Liss, Inc.