Lipase-catalyzed kinetic resolution of racemic 1-heteroarylethanols-experimental and QM/MM study

Tetrahedron Asymmetry

Volumn 19, Issue 15, 2008, Pages 1844-1852

  Toşa, Monica ^a   Pilbák, Sarolta ^b   Moldovan, Paula ^a   Paizs, Csaba ^a   Szatzker, Gábor ^b   Szakács, György ^b   Novák, Lajos ^b   Irimie, Florin Dan ^a   Poppe, László ^b  

^a BABE BOLYAI UNIVERSITY   (Romania)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1 (BENZOFURAN 3 YL)ETHANOL; 1 (BENZOTHIAZOL 2 YL)ETHANOL; 1 (BENZO[B]FURAN 3 YL)ETHANOL; 1 (BENZO[B]FURAN 3 YL)ETHYLACETATE; 1 (BENZO[B]THIOPHEN 2 YL)ETHANOL; 1 (BENZO[B]THIOPHEN 3 YL)ETHANOL; 1 (BENZO[B]THIOPHEN 3 YL)ETHYLACETATE; 1 (BENZO[D]THIAZOL 2 YL)ETHANOL; 1 (BENZO[D]THIAZOL 2 YL)ETHYLACETATE; 1 ACETOXY 1 BENZO[B]FURAN 3 YL ETHANE; 1 ACETOXY 1 BENZO[B]THIOPHEN 2 YL ETHANE; 1 ACETOXY 1 BENZO[B]THIOPHEN 3 YL ETHANE; 1 ACETOXY 1 BENZO[D]THIAZOL 2 YL ETHANE; ALCOHOL DERIVATIVE; LIPASE B;

ALCOHOLYSIS; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENANTIOSELECTIVITY; KINETICS; NONHUMAN; OPTICAL ROTATION; PRIORITY JOURNAL; RACEMIC MIXTURE; SYNTHESIS;

EID: 49349088285     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.07.004     Document Type: Article

References (46)

1. Faber K. Biotransformations in Organic Chemistry. 4th ed. (2004), Springer, Berlin
2. Rehm H.-J., Reed G., Pühler A., Stadler P., and Kelly D.R. Biotechnology: Biotransformations I and II. 2nd ed. Vols. 8a and 8b (1998), Wiley-VCH, Weinheim
3. Poppe L., and Novák L. Selective Biocatalysis: A Synthetic Approach (1992), VCH, Weinheim-New York
4. In: Liese A., Seelbach K., and Wandrey C. (Eds). Industrial Biotransformations. 2nd ed. (2006), Wiley-VCH, Weinheim-New York
5. Panke S., Held M., Wubbolts M., Schmid A., Hollmann F., Park J.B., and Bühler B. Curr. Opin. Biotechnol. 15 (2004) 272-279
6. Bornschauer U.T., and Kazlauskas R.J. Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations (2006), Wiley-VCH, Weinheim-New York
7. Ghanem A., and Aboul-Enein H.Y. Chirality 17 (2005) 1-15
8. Turner N.J. Curr. Opin. Chem. Biol. 8 (2004) 114-119
9. Paizs Cs., Toşa M., Majdik C., Moldovan P., Novák L., Kolonits P., Marcovici A., Irimie F.-D., and Poppe L. Tetrahedron: Asymmetry 14 (2003) 1495-1501
10. Paizs Cs., Toşa M., Bódai V., Szakács G., Kmecz I., Simándi B., Majdik C., Novák L., Irimie F.-D., and Poppe L. Tetrahedron: Asymmetry 14 (2003) 1943-1949
11. Yokoyama Y., Shiraishi H., Tani Y., Yokoyama Y., and Yamaguchi Y. J. Am. Chem. Soc. 125 (2003) 7194-7195
12. Cozzi P.G., and Kotrusz P. J. Am. Chem. Soc. 128 (2006) 4940-4941
13. Zaidlewicz M., Chechlowska A., Prewysz-Kwinto A., and Wojtczak A. Heterocycles 55 (2001) 569-577
14. Ravi Kumar C., Rachna S., and Palakodety R.K. Tetrahedron: Asymmetry 19 (2008) 901-905
15. Vreven T., and Morokuma K. Theor. Chem. Acc. 109 (2003) 125-132
16. Uppenberg J., Hansen M.T., Patkar S., and Jones T.A. Structure 2 (1994) 293-308
17. Uppenberg J., Patkar S., Bergfors T., and Jones T.A. J. Mol. Biol. 235 (1994) 790-792
18. Uppenberg J., Öhrner N., Norin M., Hult K., Kleywegt G.J., Patkar S., Waagen V., Anthonsen T., and Jones T.A. Biochemistry 34 (1995) 16838-16851
19. Luic M., Stefanic Z., Ceilinger I., Hodoscek M., Janezic D., Lenac T., Lescic A., Sepac D., and Tomic S. J. Phys. Chem. B 112 (2008) 4876-4883
20. Haeffner F., Norin T., and Hult K. Biophys. J. 74 (1998) 1251-1262
21. Otto R.T., Scheib H., Bornscheuer U.T., Pleiss J., Syldatk C., and Schmid R.D. J. Mol. Catal. B 8 (2000) 201-211
22. Raza S., Fransson L., and Hult K. Protein Sci. 10 (2001) 329-338
23. Ottosson J., Fransson L., and Hult K. Protein Sci. 11 (2002) 1462-1471
24. Szatzker G., Pilbák S., To{combining double acute accent}ke E.R., Bódai V., and Poppe L. FEBS J. 272 (2005) 114
25. To{combining double acute accent}ke E.R., Kolonits P., Novák L., and Poppe L. Tetrahedron: Asymmetry 17 (2006) 2377-2385
26. Bódai V., Peredi R., Bálint J., Egri G., Novák L., Szakács G., and Poppe L. Adv. Synth. Catal. 345 (2003) 811-818
27. Nagy V., To{combining double acute accent}ke E.R., Chee Keong L., Szatzker G., Ibrahim D., Che-Omar I., Szakács G., and Poppe L. J. Mol. Catal. B, Enzym. 39 (2006) 141-148
28. Rakels J.L.L., Straathof A.J.J., and Heijnen J.J. Enzyme Microb. Technol. 15 (1993) 1051-1056
29. Kazlauskas R.J., Weissfloch A.N.E., Rappaport A.T., and Cuccia L.A. J. Org. Chem. 56 (1991) 2656-2665
30. Uppenberg J., Ohmer N., Norin M., Hult K., Kleywegt G.J., Patkar S., Waagen V., Anthomen T., and Jones T.A. Biochemistry 34 (1995) 16838-16851
31. Cuiper, A. PhD thesis, University of Groningen (NL), 1999.
32. Warshel A., and Russell S. J. Am. Chem. Soc. 108 (1986) 6569-6579
33. Warshel A., Naray-Szabó G., Sussman F., and Hwang J.-K. Biochemistry 28 (1989) 3629-3637
34. Hu C.H., Brinck T., and Hult K. Int. J. Quantum Chem. 69 (1998) 89-103
35. Rotticci D., Haeffner F., Orrenius C., Norin T., and Hult K. J. Mol. Catal. B 5 (1998) 267-272
36. Orrenius C., Haeffner F., Rotticci D., Öhrner N., Norin T., and Hult K. Biocatal. Biotransf. 16 (1998) 1-15
37. Poppe L., and Novák L. Magy. Kém. Lapja 40 (1985) 366-369
38. Zaidlewicz M., Chechlowska A., Prewysz-Kwinto A., and Wojtczak A. Heterocycles 55 (2001) 569-577
39. King W.J., and Nord F.F. J. Org. Chem 13 (1948) 635-637
40. Florio S., Capriati V., and Colli G. Tetrahedron 53 (1997) 5839-5846
41. Yokoyama Y., Shiraishi H., Tani Y., and Yokoyama Y. J. Am. Chem. Soc. 125 (2003) 7194-7195
42. Noyce D.S., and Forsyth D.A. J. Org. Chem. 19 (1974) 2828-2831
43. Hill E.A., Gross M.L., Stasiewicz M., and Manion M. J. Am. Chem. Soc. 91 (1969) 7381-7392
44. HYPERCHEM 7.5, Hypercube, 2003.
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A.; gaussian 03, Revision B.05, Gaussian, Wallingford, CT, 2003.
46. gaussview, Version 3.09, R. Dennington II, T. Keith, J. Millam, K. Eppinnett, W. L. Hovell, R. Gilliland, Semichem, Shawnee Mission, KS, 2003.