Chiral recognition of alcohol enantiomers in acyl transfer reactions catalysed by Candida antarctica lipase B

Biocatalysis and Biotransformation

Volumn 16, Issue 1, 1998, Pages 1-15

  Orrenius, Christian ^a   Hæffner, Fredrik ^a   Rotticci, Didier ^a   Öhrner, Niklas ^a   Norin, Torbjörn ^a   Hult, Karl ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

CALB; Chiral recognition; Molecular modelling; Sec alcohol enantiomers; Transesterification

Indexed keywords

ALCOHOL; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; CANDIDA; CHEMICAL REACTION KINETICS; CHIRALITY; CONTROLLED STUDY; ENANTIOMER; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; MOLECULAR DYNAMICS; MOLECULAR MODEL;

CANDIDA; CANDIDA ANTARCTICA;

EID: 0031965757     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.3109/10242429809040107     Document Type: Article

References (27)

1. Berglund, P., Holmquist, M., Hedenström, E., Hult, K. and Högberg, H.-E. (1993) 2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa: Alcohol chain length and enantioselectivity. Tetrahedron Asymmetry, 4(8), 1869-78.
2. Besler, B.H., Merz Jr., K.M., and Kollman, P.A. (1990). Atom charges derived from semiempirical methods. J. Comput. Chem., 11, 431-439.
3. de Zoete, M., Kock-van Dalen, A., van Rantwijk, F. and Sheldon, R. (1993). Ester ammoniolysis: a new reaction. J. Chem. Soc., Chem. Comm., 1831.
4. Fersht, A. (1985). Enzyme Structure and Mechanism (2nd ed.). New York: Freeman and company.
5. Frykman, H., Öhrner, N., Hult, K. and Norin, T. (1993). S-Ethyl thiooctanoate as acyldonor in lipase-catalysed resolution of secondary alcohols. Tetrahedron Letters, 34, 1367-1370.
6. Kazlauskas, R.J., Weissfloch, A.N., Rappaport, A.T. and Cuccia, L.A. (1991) A rule to predict wich enantiomer of a secondary alcohol reacts faster in reactions by cholsterol esterase, Pseudomonas cepacia and Candida rugosa lipase, J. Org. Chem., 56, 2656-2665.
7. Martinelle, M., Holmquist, M. and Hult, K. (1995). On the interfacial activation of Candida antarctica lipase A and B as compared with Humicola lanugmosa lipase. Biochimica et Biophysica Acta, 1259, 272-276.
8. Martinelle, M. and Hult, K. (1995). Kinetics of acyl-transfer reactions in organic media catalysed by Candida antarctica lipase B. Biochimica et Biophysica Acta, 1251, 191-197.
9. 2-symmetry by lipase catalysed alcoholysis and aminolysis. Acta Chem. Scand., 50, 918-921.
10. 2-symmetry by lipase catalysed transesterinfication Tetrahedron: Asymmetry, 4, 925.
11. Nicolas, A., Egmond, M., Verrips, T., de Vlieg, J., Longhi, S., Cambillau, C. and Martinez, C. (1996). Contribution of cutinase serine 42 side chain to the stabilization of the oxyanion transition state. Biochemistry, 35, 398-410.
12. Norin, M., Haeffner, F., Hult, K. and Edholm, O. (1994). Molecular dynamics simulations of an enzyme surrounded by vacuum, water or a hydrophobic solvent. Biophys. J., 67, 548.
13. Norin, M., Matson, A., Hult, K. and Norin, T. (1993). Molecular modelling of chymotrypsin-substrate interactions: Calculation of enantioselectivity. Biocatalysis, 7, 131-147.
14. O'Hagan, D. and Zaidi, N. (1992). Hydrolytic resolution of tertiary acetylenic acetate esters with the lipase from Candida cylindracea. J. Chem. Soc., Perkin Trans. 1, 947. The authors found low enantioselectivity in the hydrolysis of tertiary acetylenic esters.
15. Ollis,D.L., Cheah, E., Cygler, M., Dijkstra, B., Frolow, F., Franken, S., Harel, M., Remington, S., Silman, I., Schrag, J., Sussman, J., Verscheuren, K and Goldman, A. (1992). The α/β hydrolase fold. Protein Eng., 5, 197-211.
16. Orrenius, C., Norin, T., Hult, K. and Carrea, G. (1995a). The Candida antarctica lipase B catalysed kinetic resolution of seudenol in non-aqueous media of controlled water activity. Tetrahedron: Asymmetry, 6(12), 3023-3030.
17. Orrenius, C., Öhrner, N., Rotticci, D., Mattson, A., Hult, K. and Norin, T. (1995b). Candida antarctica lipase B catalysed kinetic resolution: Substrate structure requirements for the preparation of enantiomerically enriched secondary alcohols. Tetrahedron. Asymmetry, 6(5), 1217-1220.
18. Pozo, M., Pulido, R. and Gotor, V. (1992). Vinyl carbonates as novel alkopxycarbonylation reagents in enzymatic synthesis of carbonates. Tetrahedron, 48(31), 6477-6484.
19. Rakels, J.L.L., Straathof, A.J.J. and Heijnen, J J. (1993). A simple method to determine the enantiomeric ratio in enantioselective biocatalysis. Enzyme Microb. Technol., 15, 1051.
20. Santaniello, E., Ferraboschi, P., Grisenti, P. and Manzocchi, A. (1992). The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem. Rev., 92, 1071-1140.
21. Tripos (1994). SYBYL, version 6.1, St Lousi, Missouri.
22. Uppenberg, J., Trier Hansen, M., Patkar, S. and Jones, A. (1994). The sequence, crystal structure determination and refinement of two crystal forms of lipase B from Candida antarctica. Structure, 2 (april), 293-308.
23. Uppenberg, J., Öhrner, N., Norin, M., Hult, K., Kleywegt, G.J., Patkar, S., Waagen, V., Anthonsen, T. and Jones, A.T. (1995). Crystallographic and molecular-modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols. Biochemistry, 34, 16838-16851.
24. Waagen, V., Hollingsaeter, I., Partali, V., Thorstad, O. and Anthonsen, T. (1993). Enzymatic resolution of butanoic esters of 1-phenyl, 1-phenylmethyl, 1-[2-phenylethyl] and 1-[2-phenoxyethyl] ethers of 3-methoxy-1,2-propanediol Tetrahedron: Asymmetry, 4, 961-968.
25. Weiner, S.J., Kollman, P.A., Case, D.A., Singh, U C., Ghio, C., Alagona, G., Profeta, S.J. and Weiner, P. (1984), A new force field for molecular mechanical simulation, of nucleic acids and proteins J. Am. Chem Soc., 106, 765-784.
26. Weissfloch, A.N.E. and Kaslauskas, R.J. (1995) Enantiopreference of lipase from Pseudomonas cepacia toward primary alcohols. J. Org. Chem., 60, 6959-6969.
27. Öhrner, N., Martinelle, M., Mattson, A., Norin, T. and Hult, K. (1992). Displacement of the equilibrium in lipase catalysed transesterification in ethyl octanoate by continous evaporation of ethanol. Biotechnology Letters, 14, 263-268.