engleski

Enantioselectivity of Burkholderia cepacia lipase towards primary and secondary alcohols: molecular modelling and 3D QSAR analysis

Because of their broad substrate specificity and high enantioselectivity, microbial lipases are important targets for exploitation as biocatalysts. The aim of this study was to elucidate lipase-catalysed reactions at the sub-molecular level in order to improve their application in syntheses of enantiomerically pure products. We performed a detailed molecular modelling on complexes of tetrahedral intermediates (TIs) of six primary and seventeen secondary alcohols (all with an aromatic ring) with Burkholderia cepacia lipase (BCL) in the reaction of esterification, for which experimental measurements were available. For secondary alcohols R = substituted phenyl ring, X = OH, X1 = OAc, Y = Y1 = OAc and for primary alcohols R = an aryl ring, X = X1 = CH3, Y = OH, Y1 = OAc.

lipase, COMBINE analysis, enantioselectivity, QSAR

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