Stereo- and enantioselectivity of the soluble epoxide hydrolase-catalysed hydrolysis of (±)-cis-dialkyl substituted oxiranes

✍ Scribed by Cinzia Chiappe; Consiglia Doriana Palese

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 430 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00657-2

✦ Synopsis

Both enantiomers of cis-(+)-2,3-epoxyheptane (la), cis-3,4-epoxyheptane (lb), cis-3,4epoxynolmne (It) cis-3,4-epoxynonan¢-l-ol (ld) and cis-l-methoxy-3,4-epoxynonane (le) are transformed into the corresponding threo-diols 2a--e by soluble epoxide hydrolaso catalysed hydrolysis. The reaction proceeds with a substrate and product enantioselection, which is highly dependent on the substituents at the oxirane ring. Whereas the hydrolysis of racemic la shows practically no enantioselection, that of its isomer lb, gives after complete hydrolysis, in a stereoconvergent way, the corresponding threo-diol (3R,4R)-2b. On the other hand, the hydrolysis of epoxides 1c..¢ progress with a fairly good (1¢ and le) or complete (ld) substrate enantioselection to give racemic (2c) or, in a stereoconvergent way, optically enriched (2e) or pure (2d) diols. Significant differences were observed from the previous results of the hydrolysis of the same substrates with microsomal epoxide hydrelase.