12
Views
11
CrossRef citations to date
0
Altmetric
Original Article

On the Prediction of the Enantioselectivity of Candida rugosa Lipase by Comparative Molecular Field Analysis

, , &
Pages 227-239 | Published online: 11 Jul 2009

References

  • Chen C. S., Fujimoto Y., Girdaukas G., Sih C. J. Quantitative Analysis of Biochemical Kinetic Resolutions of Enantiomers. J. Am. Chem. Soc. 1982; 104: 7294–7299
  • Cramer R, Jr., Patterson D. E., Bunce J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988; 110: 5959–5967
  • Cygler M., Schrag J. D., Sussman J. L., Harel M, Silman I., Gentry M. K., Doctor B. D. Relationship between sequence conservation and three-dimensional structure in a large family of esterases, lipases. and related proteins. Protein Science 1993; 2: 366–382, and references therein
  • Faber K. Hydrolytic Reactions. Biotransformations in Organic Chemistry. Springer, Berlin 1992; 70–72
  • Fersht A. Enzyme-Substrate Complementarity and the use of Binding Energy in Catalysis and Specificity and Editing Mechanisms. Enzyme Structure and Mechanism. W.H. Freeman and Company, New York 1977; 98–367
  • Fitzpatrick P. A., Ringe D., Klibanov A. M. Computer-Assisted Modeling of Subtilisin Enantioselectivity in Organic Solvent. Biotechnol. Bioeng. 1992; 40: 735–742
  • Geladi P., Kowalski B. R. Partial Least Squares Regression: A Tutorial. Anal. Chim. Acta 1986; 185: 1–17
  • Grochulski P., Li Y., Schrag J., Bouthillier F., Smith P., Harrison D., Rubin B., Cygler M. Insights into Interfacial Activation from an Open Structure of Candida rugosa Lipase. J. Biol. Chem. 1993; 268: 12843–12847
  • Hirose Y., Anzai M., Saitoh M, Naemura K., Chikamatsu H. Absolute Configuration of Optically Active Tricyclo[2.2.l.02, 6]heptan-3-ol (Nortricyclanol). An Enhancement of Enantiomeric Purity of a Chiral Alcohol by Repeating Enzymatic Kinetic Resolution. Chem. Lett. 1989; 1939–1942.
  • Kazlaukas R., Weissfloch A. N.E., Rappaport A. T., Cuccia L. A. A Rule To Predict Which Enantiomer of a Secondary Alcohol Reacts Faster in Reactions Catalyzed by Cholesterol Esterase, Lipase from Pseudomonas cepacia, and Lipase from Candida rugosa. J. Org. Chem. 1991; 56: 2656–2665
  • Klebe G., Abraham U. On the Prediction of Binding Properties of Drug Molecules by Comparative Molecular Field Analysis. J. Med. Chem. 1993; 36: 70–80
  • Königsberger K., Faber K., Marschner Ch., Penn G., Baumgartner P., Griengl H. Enzymatic Resolution of endo-Bicyclo[2.2.1]hept-2-yl Butyrates and Related Compounds: Steric Requirement in the Bridge-Region. Tetrahedron 1989; 45: 673–680
  • Longhi S., Lotti M., Fusetti F., Pizzi E., Tramontana A., Alberghina L. Homology-derived three-dimensional structure prediction of Candida Cylindracea lipase. Biochim. Biophys. Acta 1992; 1165: 129–133
  • Norin M., Hult K., Mattson A., Norin T. Molecular Modelling of Chymotrypsin-Substrate interactions: Calculation of Enantioselectivity. Biocatalysis 1993; 7: 131–147
  • Oberhauser Th., Faber K., Griengl H. A substrate model for the enzymatic resolution of esters of bicyclic alcohols by Candida cylindracea lipase. Tetrahedron 1989; 45: 1679–1682
  • Oberhauser Th., Bodenteich M., Faber K., Penn G., Griengl H. Enzymatic resolution of norbornanetype esters. Tetrahedron 1987; 43: 3931–3944
  • Ortiz de Montellano P. R., Fruetel J. A., Collins J. R., Camper D. L., Loew G. H. Theoretical and Experimental Analysis of the Absolute Stereochemistry of cis-β-Methylenstyrene Epoxidation by Cytochrom P450. J. Am. Chem. Soc. 1991; 113: 3195–3196
  • Poppe L., Novak L. Hydrolyses: Preparative Biocatalysis. Selective Biocatalysis. Verlag Chemie. 1992; 67–157
  • Saf R., Faber K., Penn G., Griengl H. Enzymatic preparation of optically active 7-Oxabicy-clo[2.2.1]heptane derivatives. Tetrahedron 1988; 44: 389–392
  • Vinter J. G., Davis A., Saunders M. R. Strategic Approaches to Drug Design I. An Integrated Software Framework for Molecular Modelling. J. Comput.-Aided Mol. Des. 1987; 1: 31–35
  • Warshel A., Naray-Szabo G., Sussman F., Hwang J.-K. How Do Serine Proteases Really Work. Biochemistry 1989; 28: 3630–3637
  • Wold S., Albano C, Dunn W.J., Jr., Edlund U., Esbensen K., Geladi P., Hellberg S., Johansson E., Lindberg W., Sjöstróm M. Multivariate Data Analysis in Chemistry. Chemometrics 1984; 17–95.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.