Enantioselective lipase-catalysed kinetic resolution of acyloxymethyl and ethoxycarbonylmethyl esters of 1,4-dihydroisonicotinic acid derivatives

Tetrahedron Asymmetry

Volumn 13, Issue 21, 2002, Pages 2389-2397

  Sobolev, Arkadij ^a,b   Franssen, Maurice C R ^a   Poikans, Janis ^b   Duburs, Gunars ^b   De Groot, Aede ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; ETHER DERIVATIVE; LIPASE B; NICOTINIC ACID DERIVATIVE;

ARTICLE; CANDIDA ANTARCTICA; CATALYST; CRYSTALLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; KINETICS; PRIORITY JOURNAL; STEREOSPECIFICITY; TEMPERATURE;

EID: 0037206735     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00655-9     Document Type: Article

References (28)

1. Klusa V., Duburs G. Acta Medica Baltica. 3:1996;104-114.
2. Klusa V., Germane S. Scand. J. Lab. Anim. Sci. 23:1996;403-409.
3. Misane I., Klusa V., Dambrova M., Germane S., Duburs G., Bisenieks E., Rimondini R., Ogren S.O. Eur. Neuropsychopharmacol. 8:1998;329-347.
4. Tarasenko L.M., Neporada K.S., Klusha V. Bull. Exp. Biol. Med. 133:2002;369-371.
5. Mannhold R. Drugs Today. 30:1994;103-122.
6. Tokuma Y., Noguchi H. J. Chromatogr. A. 694:1995;181-193.
7. Ashimori A., Uchida T., Ohtaki Y., Tanaka M., Ohe K., Fukaya C., Watanabe M., Kagitani M., Yokoyama K. Chem. Pharm. Bull. 39:1991;108-111.
8. Peri R., Padmanabhan S., Rutledge A., Singh S., Triggle D.J. J. Med. Chem. 43:2000;2906-2914.
9. Kongsamut S., Kamp T.J., Miller R.J., Sanguinetti M.C. Biochem. Biophys. Res. Commun. 130:1985;141-148.
10. van Zwieten P.A. Blood Press. Suppl. 1:1998;5-8.
11. Beudeker H.J., van der Velden J.W., van der Aar E.M. Int. J. Clin. Pract. Suppl. 114:2000;36-40.
12. Achiwa K., Kato T. Curr. Org. Chem. 3:1999;77-106.
13. Marchalin S., Chudik M., Mastihuba V., Decroix B. Heterocycles. 48:1998;1943-1957.
14. Sih C.J., Gu S.Q., Holdgrun X., Harris K. Chirality. 4:1992;91-97.
15. de Castro M.S., Salazar L., Sinisterra J.V. Tetrahedron: Asymmetry. 8:1997;857-858.
16. Sobolev A., Franssen M.C.R., Vigante B., Cekavicus B., Zhalubovskis R., Kooijman H., Spek A.L., Duburs G., de Groot Ae. J. Org. Chem. 67:2002;401-410.
17. Sobolev A., Franssen M.C.R., Vigante B., Cekavicus B., Makarova N., Duburs G., de Groot Ae. Tetrahedron: Asymmetry. 12:2001;3251-3256.
18. Hirose Y., Kariya K., Sasaki I., Kurono Y., Ebiike H., Achiwa K. Tetrahedron Lett. 33:1992;7157-7160.
19. Faber K. Biotransformations in Organic Chemistry. 3rd ed. 1997;402 Springer-Verlag, Berlin, Heidelberg.
20. Franssen M.C.R., Goetheer E.L.V., Jongejan H., de Groot Ae. Tetrahedron Lett. 39:1998;8345-8348.
21. Brunet C., Zarevucka M., Wimmer Z., Legoy M.D. Biotechnol. Lett. 21:1999;605-610.
22. Kalninsh A., Baumane L., Stradinsh J., Bisenieks E., Poikans J., Uldrikis J., Duburs G. Latv. J. Chem. 1998;71-76.
23. Holdgrun X.K., Sih C.J. Tetrahedron Lett. 32:1991;3465-3468.
24. Sobolev A., Franssen M.C.R., Makarova N., Duburs G., de Groot Ae. Tetrahedron: Asymmetry. 11:2000;4559-4569.
25. Chekavichus B.S., Sausins A.E., Dubur G.J. Khim. Geterotsikl. Soed. 1982;1072-1077.
26. Chen C.S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294-7299.
27. Rakels J.L.L., Straathof A.J.J., Heijnen J.J. Enzyme Microb. Technol. 15:1993;1051-1056.
28. Jongejan J.A., van Tol J.B.A., Geerlof A., Duine J.A. Recl. Trav. Chim. Pays-Bas. 110:1991;247-254.