Original scientific paper

Enantioselectivity of Pseudomonas cepacia Lipase towards 2-Methyl-3(or 4)-arylalkanols: An Approach Based on the Stereoelectronic Theory and Molecular Modeling

Sanja Tomić orcid.org/0000-0002-0550-0878 ; Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Vladimir Dobovičnik ; Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Vitomir Šunjić ; Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia
Biserka Kojić-Prodić ; Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia

Abstract

For a better understanding of the previously reported enantioselectivity of Pseudomonas cepacia lipase (PCL) in acylation of racemic primary alcohols, 2-methyl-3(or 4)-arylalkanols, molecular modeling of tetrahedral intermediates (TIs) at the active site was performed. The most probable conformers of TIs were elucidated and their interactions with the amino acid residues of the binding pockets at the enzyme active site were studied. The free energy difference between TIs of two enantiomers was approximated by the differences in potential energy and the solvent accesible surface area. Correlation between the Hε(His286)- Oγ(Ser87) hydrogen bond differences of diastereomeric, low energy gauche-TIs, and experimentally determined enantiomeric ratios was found. In agreement with the stereoelectronic theory, the gauche-TI precedes ester release.

Keywords

Pseudomonas cepacia lipase; kinetic resolution; primary alcohols; enantioselectivity; molecular modeling; stereoelectronic theory

Hrčak ID:

131827

URI

https://hrcak.srce.hr/131827

Publication date:

2.4.2001.

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