Elsevier

Tetrahedron

Volume 44, Issue 9, 1988, Pages 2575-2582
Tetrahedron

Substrate specificity and enantioselectivity of penicillinacylase catalyzed hydrolysis of phenacetyl esters of synthetically useful carbinols

https://doi.org/10.1016/S0040-4020(01)81708-7Get rights and content

Abstract

Penicillinacylase from E.coli, immoblized on Eupergit C beads catalyzes the hydrolysis in water/CH3CN 10:1, at pH 7.5 and 23° C, of a set of O-phenylacetate esters of primary carbinols. The highest enantioselectivity is observed in the case of the 2,2-dimethyl-1,3-dioxolane-4-methanols structurally related to the penicillin (1) framework. Minor modifications of this basic structure are not altering the acceptability by the enzyme, but significantly decrease the enantioselectivity of the hydrolysis, as does the use of benzene as solvent and sepharose-bound enzyme.

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