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- W2031272034 abstract "Abstract Computer-aided molecular modeling was performed to investigate the experimentally determined enantioselectivities of Pseudomonas cepacia lipase (PCL) toward various saturated γ- and δ-lactones. Experimental data indicated that PCL preferentially hydrolyzes the ( R )-enantiomers of both types of substrates. Interactions between the non-polar aliphatic alkyl chain of the ( S )-enantiomers and the polar side chain of residue Y29 were identified to mediate enantioselectivity. Upon binding, the tyrosine was displaced, thus initiating a cascade of local geometry changes which led to the breakdown of the essential H-bond network at the active site H286. The lactone ring of the ( S )-δ-enantiomers further added to this process, since it was forced into an unfavorable position by repulsion from Y29, directly affecting the position of H286. In contrast, the respective ( R )-enantiomers fit without distorting side chains essential for catalysis in the binding pocket of PCL. In δ-lactones, the stereocenter was located close to the imidazole ring of H286, suggesting a more intense interaction with H286 as compared to γ-lactones. The length of the aliphatic chain adjacent to the stereocenter also affected the enantiopreference toward hydrolysis of δ-lactones, while for γ-lactones, the enantioselectivity did not significantly change with increasing alkyl chain length. In the cases of ( S )-δ-octa- and ( S )-δ-nonalactone, two alternative possible binding modes were examined, indicating that the respective substrate resolutions led to poor enantioselectivity as compared to the longer-chain δ-lactone substrates." @default.
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- W2031272034 date "2000-10-01" @default.
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- W2031272034 title "Computer-aided molecular modeling of the enantioselectivity of Pseudomonas cepacia lipase toward γ- and δ-lactones" @default.
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- W2031272034 doi "https://doi.org/10.1016/s1381-1177(00)00129-6" @default.
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