The epoxide hydrolase catalyzed hydrolysis of trans-3-bromo-1,2-epoxycyclohexane. A direct proof for a general base catalyzed mechanism of the enzymatic hydration
1981; Elsevier BV; Volume: 102; Issue: 3 Linguagem: Inglês
10.1016/0006-291x(81)91614-4
ISSN1090-2104
AutoresGiuseppe Bellucci, Giancarlo Berti, Maria Enrica Ferretti, Franco Marioni, Franca Re,
Tópico(s)Enzyme Catalysis and Immobilization
ResumoThe hydrolysis of (±)-trans-3-bromo-1,2-epoxycyclohexane in the presence of rabbit liver microsomes was investigated, and found to yield, beside c-3-bromocyclohexane-r-1,t-2-diol, 2,3-epoxycyclohexanol. It was demonstrated that the latter compound was the only product of the enzymatic reaction, whereas the diol resulted from a non enzymatic hydration in the reaction medium. These data provide the first direct proof for a general base catalysis in the enzymatic epoxide hydration, previously hypothesized on the basis of several lines of indirect evidence, and disprove alternative mechanisms involving protonation of the oxirane oxygen.
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