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Enantiorecognition of chiral acids by Candida rugosa lipase: Two substrate binding modes evidenced in an organic medium
KTH, School of Biotechnology (BIO), Biochemistry.ORCID iD: 0000-0002-9577-832X
2001 (English)In: American Chemical Society Symposium Series (ACS), ISSN 0097-6156, E-ISSN 1947-5918, Vol. 776, 263-273 p.Article in journal (Refereed) Published
Abstract [en]

We have identified the existence of different modes of binding the enantiomers of 2-methyl-branched carboxylic acids to a lipase active site by rational substrate engineering. Similar to hydrolysis, previously investigated, we have now evidence for differential binding modes in the Candida rugosa lipase-catalyzed esterifications in cyclohexane. The relevance of considering two different binding modes to understand lipase enantiorecognition is demonstrated by introducing bulky substituents on a chiral carboxylic acid which impose a different orientation of the substrate acyl chain in the active site of Candida rugosa lipase. With this substrate engineering approach based on molecular modeling it is thus possible to markedly alter the enantioselectivity of the lipase. Examples from hydrolysis and new results from esterifications in an organic solvent are presented and discussed.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2001. Vol. 776, 263-273 p.
National Category
Biocatalysis and Enzyme Technology
Identifiers
URN: urn:nbn:se:kth:diva-74862OAI: oai:DiVA.org:kth-74862DiVA: diva2:490133
Note
References: Wong, C.-H., Whitesides, G.M., Enzymes in synthetic organic chemistry (1994) Tetrahedron Organic Chemistry Series, 12. , Pergamon: Oxford, U.K; Faber, K., (1997) Biotransformations in Organic Chemistry, 3rd Ed., , Springer: Berlin, Germany; Rubin, B., Dennis, E.A., Lipases part B (1997) Methods in Enzymology, 286, pp. 1-563. , Academic Press: New York; Kazlauskas, R.J., Bornscheuer, U.T., (1998) Biotechnology, 2nd Ed., 8 A, pp. 37-191. , Biotransformations I; Kelly, D. R., Ed.; Wiley: Weinheim, Germany; Berglund, P., Huit, K., (1999) Stereoselective Biocatalysis, pp. 633-657. , Patel, R., Ed.; Marcel Dekker: New York, in press; Schmid, R.D., Verger, R., (1998) Angew. Chem. Int. Ed. Engl., 37, pp. 1609-1633; Reetz, M.T., Zonta, A., Schimossek, K., Liebeton, K., Jaeger, K.-H., (1997) Angew. Chem. Int. Ed. Engl., 36, pp. 2830-2832; Arnold, F.H., Volkov, A.A., (1999) Curr. Opin. Chem. Biol., 3, pp. 54-59; Nixon, A.E., Ostermeier, M., Benkovic, S.B., (1998) Trends Biotechnol., 16, pp. 258-264; Holmquist, M., Berglund, P., (1999) Org. Lett., 1, pp. 763-765; Högberg, H.-E., Berglund, P., Edlund, H., FÀgerhag, J., Hedenström, E., Lundh, M., Nordin, O., Vörde, C., (1994) Catalysis Today, 22, pp. 591-606; Sheldon, R.A., (1993) Chirotechnology: Industrial Synthesis of Optically Active Compounds, , Marcel Dekker: New York; Bydén, M., Edlund, H., Berglund, P., Lindström, B., (1997) Prog. Colloid. Polym. Sci., 105, pp. 360-364; Berglund, P., Holmquist, M., Hedenström, E., Hult, K., Högberg, H.-E., (1993) Tetrahedron: Asymmetry, 4, pp. 1869-1878; Berglund, P., Holmquist, M., Hult, K., Högberg, H.-E., (1995) Biotechnol. Lett., 17, pp. 55-60; Berglund, P., Hedenström, E., (1999) Enzymes in Non-aqueous Media: IV Synthetic Aspects, , Holland, H., Ed.; Methods in Biotechnology; Humana Press: Totowa, NJ, In Press; Edlund, H., Berglund, P., Jensen, M., Hedenström, E., Högberg, H.-E., (1996) Acta Chem. Scand., 50, pp. 666-671; Holmquist, M., HÊffner, F., Norm, T., Hult, K., (1996) Protein Sci., 5, pp. 83-88; Grochulski, P., Bouthillier, F., Kazlauskas, R.J., Serreqi, A.N., Schrag, J.D., Ziomek, E., Cygler, M., (1994) Biochemistry, 33, pp. 3494-3500; Berglund, P., Holmquist, M., Hult, K., (1998) J. Mol. Catal. B: Enzym., 5, pp. 283-287; Holmberg, E., Holmquist, M., Hedenström, E., Berglund, P., Norin, T., Högberg, H.-E., Hult, K., (1991) Appl. Microbiol. Biotechnol., 35, pp. 572-578; Chen, C.-S., Fujimoto, Y., Girdaukas, G., Sih, C.J., (1982) J. Am. Chem. Soc., 104, pp. 7294-7299; Van Tol, J.B.A., Jongejan, J.A., Geerlof, A., Duine, J.A., (1991) Recl. Trav. Chim. Pays-Bas, 110, pp. 255-262; Rakels, J.L.L., Straathof, A.J.J., Heijnen, J.J., (1993) Enzyme Microb. Technol., 15, pp. 1051-1056; Noyce, D.S., Denney, D.B., (1950) J. Am. Chem. Soc., 72, pp. 5743-5745; Sonnet, P.E., (1982) J. Org. Chem., 47, pp. 3793-3796; Sonnet, P.E., (1987) J. Org. Chem., 52, pp. 3477-3479; Guanti, G., Narisano, E., Podgorski, T., Thea, S., Williams, A., (1990) Tetrahedron, 46, pp. 7081-7092; Hedenström, E., Department of Chemistry and Process Technology, Mid Sweden University, Sundsvall, Sweden; Unpublished ResultsFieser, L.F., Fieser, M., (1967) Reagents for Organic Synthesis, 1, p. 142. , Wiley: New York NR 20140805Available from: 2012-02-03 Created: 2012-02-03 Last updated: 2017-12-08Bibliographically approved

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