Steric requirements for the active site of a lipase from Candida rugosa studied by the use of a sulfinyl group as a chiral probe

Biocatalysis and Biotransformation

Volumn 16, Issue 2, 1998, Pages 163-180

  Löwendahl, A Christina ^a   Allenmark, Stig G ^a,b  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b Department of Chemistry ^*  (Sweden)

Author keywords

Candida rugosa; Ester hydrolysis; Kinetic resolution; Lipases; Sulfinyl group; Sulfoxides

Indexed keywords

CATALYST ACTIVITY; CATALYST SELECTIVITY; CHEMICAL BONDS; ENZYME KINETICS; ESTERS; HYDROLYSIS; MOLECULAR STRUCTURE; REACTION KINETICS;

LIPASES; SULFOXIDES;

SULFUR COMPOUNDS;

BENZOIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA RUGOSA; CHEMICAL STRUCTURE; HYDROLYSIS; ISOELECTRIC POINT; MOLECULAR MODEL; NONHUMAN;

ASPERGILLUS NIGER; CANDIDA ANTARCTICA; CANDIDA RUGOSA; PSEUDOMONAS; PSEUDOMONAS SP.;

EID: 0031805360     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.3109/10242429809003619     Document Type: Article

References (27)

1. Allenmark, S. and Hagberg, C.-E (1970) Anchimerically assisted sulfoxide reactions. V. Assisted racemization of optically active 2-methylsulfinylbenzoic acid. Acta Chem. Scand., 24, 2225-2231.
2. Allenmark, S and Andersson, S. (1992a) Some mechanistic aspects on chiral discrimination of organic acids by immobilized bovine serum albumin (BSA). Chirality, 4, 24-29.
3. Allenmark, S. and Ohlsson, A (1992b) Studies of the heterogeneity of a Candida cylindracea (rugosa) lipase: Monitoring of esterolytic activity and enantioselectivity by chiral liquid chromatography. Biocatalysis, 6, 211-221.
4. Allenmark, S.G. and Andersson, A.C. (1993) Lipase-catalyzed kinetic resolution of a series of esters having a sulfoxide group as the stereogenic group. Tetrahedron. Asymmetry, 4, 2371-2376.
5. Allenmark, S., Andersson, S , Möller, P. and Sanchez, D. (1995a) A new class of network-polymeric chiral stationary phases Chirality, 7, 248-256.
6. Allenmark, S., Andersson, C and Widell, P (1995b) Chromatographic resolution of some cyclic sulfoximides derived from prochiral and chiral sulfoxides Chirality, 7, 541-546.
7. Allenmark, S. and Claeson, S. (1996) Resolution and chiroptical properties of a diaryl diacyloxy spirosulfurane with six-membered spiro rings Enantiomer, 1, 423-428.
8. Bohman, O. and Allenmark, S. (1973) The solvolytic behaviour of optically active S-(carboxyphenyl)-S-methyl-N-(p-tosyl)-sulfimide. Chem. Ser , 4, 202-206.
9. Burgess, K , Henderson, I. and Ho, K.-K. (1992) Biocatalytic resolutions of sulfinylalkanoates: A facile route to optically active sulfoxides J. Org. Chem., 57, 1290-1295.
10. Cardellicchio, C., Naso, F. and Scilimati, A. (1994) An efficient biocatalyzed kinetic resolution of methyl (Z)-3-arylsulphinylpropenoates. Tetrahedron Lett . 35, 4635-4638.
11. Carreño, M.C. (1995) Applications of sulfoxides to asymmetric synthesis of biologically active compounds. Chem. Rev., 95, 1717-1760.
12. Chen, C.-S., Fujimoto, Y., Girdaukas, G and Sih, C.J. (1982) Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am Chem. Soc., 104, 7294-7299.
13. Desnuelle, P. (1972) The lipases. In The Enzymes, Vol. 7, ed. Boyer, P.D., 3rd edn , pp. 575-616. New York, London: Academic Press.
14. Faber, K. (1992) Biotransformations in organic chemistry, pp 72-76. Berlin Springer-Verlag
15. Grochulski, P., Li, Y., Schrag, J D., Bouthilher, F . Smith, P., Harrison, D., Rubin, B and Cygler, M. (1993) Insights into interfacial activation from an open structure of Candida rugosa lipase. J Biol. Chem., 268, 12843-12847.
16. Grochulski, P., Bouthillier, F , Kazlauskas, R.J., Serreqi, A.N., Schrag, J.D , Ziomek, E. and Cygler, M (1994) Analogs of reaction intermediates identify a unique substrate binding site in Candida rugosa lipase. Biochemistry, 33, 3494-3500.
17. Holland, H.L. (1988) Chiral sulfoxidation by biotransformation of organic sulfides Chem. Rev., 88, 473-485
18. Kapovits, I., Rábai, J., Ruff, F and Kucsman, A. (1979) Diaryldiacyloxyspirosulfuranes-II Synthesis from sulfoxides and hydrolysis. Tetrahedton, 35, 1875-1881.
19. Kusters, E. and Gerber, G. (1997) Enantiomeric separation of racemic sulphoxides on chiral stationary phases by gas and liquid chromatography. Chromatographia, 44, 91-96.
20. Mikolajczyk, M. and Drabowicz, J. (1982) Chiral organosulfur compounds. Top. Stereochem., 13, 333-468
21. Mikolajczyk, M., Kielbasinski, P., Zurawinski, R., Wieczorek, M W and Blaszczyk, J. (1994) A novel enzymatic approach to the synthesis of chiral sulfoxides: Enzymatic hydrolysis of prochiral sulfinyldicarboxylates. Synlett, 127-129.
22. Ohta, H., Kato, Y. and Tsuchihashi, G-I. (1986) Enzyme mediated synthesis of optically active ω-arenesulfinylalkanoic esters. Chem. Lett., 217-218.
23. Pitchen, P and Kagan, H.B. (1984) An efficient asymmetric oxidation of sulfides to sulfoxides. Tetrahedron Lett., 25, 1049-1052.
24. Serreqi, A.N and Kazlauskas, R.J. (1995) Kinetic resolution of sulfoxides with pendant acetoxy groups using cholesterol esterase Substrate mapping and an empirical rule for chiral phenols. Can. J. Chem , 73, 1357-1367.
25. Solladié, G. (1981) Asymmetric synthesis using nucleophilic reagents containing a chiral sulfoxide group. Synthesis, 185-196.
26. Tamai, S., Miyauchi, S. Morizane, C., Miyagi, K., Shimizu, H., Kume, M., Sano, S., Shiro, M. and Nagao, Y. (1994) Enzymatic hydrolyses of the σ-symmetric dicarboxylic diesters bearing a sulfinyl group as the prochiral center. Chem. Lett , 2381-2384
27. Wu, S -H., Guo, Z.-W. and Sih, C.J. (1990) Enhancing the enantioselectivity of Candida lipase catalyzed ester hydrolysis via noncovalent enzyme modification. J. Am. Chem. Soc , 112, 1990-1995.