Transformation of racemic ethyl 3-hydroxybutanoate into the (R)-enantiomer exploiting lipase catalysis and inversion of configuration

Tetrahedron Asymmetry

Volumn 18, Issue 14, 2007, Pages 1682-1687

  Turcu, Mihaela C ^a   Kiljunen, Eero ^b   Kanerva, Liisa T ^a  

^a UNIVERSITY OF TURKU   (Finland)

^b ORION CORPORATION   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALCOHOL; BUTYRIC ACID DERIVATIVE; CESIUM; ETHYL 3 HYDROXYBUTANOATE; ETHYL ACETOXYBUTANOATE; ISOPROPENYL ACETATE; LIPASE B; PROPYLENE; UNCLASSIFIED DRUG;

ACYLATION; ALCOHOLYSIS; ARTICLE; CANDIDA ANTARCTICA; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 34548032574     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.06.030     Document Type: Article

References (19)

1. Bush K., Macielag M., and Weidner-Wells M. Curr. Opin. Microbiol. 7 (2004) 466-476
2. Kobayashi R., Konomi M., Hasegawa K., Morozumi M., Sunakawa K., and Ubukata K. Antimicrob. Agents Chemother. 49 (2005) 889-894
3. Dahloff A., Janjic N., and Echols R. Biochem. Pharmacol. 71 (2006) 1085-1095
4. Berks A.H. Tetrahedron 52 (1996) 331-375
5. Ham W.-H., Oh C.-Y., Lee Y.-S., and Jeong J.-H. J. Org. Chem. 65 (2000) 8372-8374
6. Inoue K., Makino Y., and Itoh N. Tetrahedron: Asymmetry 16 (2005) 2539-2549
7. Ribeiro J.B., Ramos M.C.K., Aquino Neto F.R., Leite S.G.F., and Antunes O.A.C. J. Mol. Cat. B: Enzym. 24-25 (2003) 121-124
8. Rodriguez S., Schroeder K.T., Kayser M.M., and Stewart J.D. J. Org. Chem. 65 (2000) 2586-2587
9. Kometani T., Yoshii H., Kitatsuji E., Nishimura H., and Matsuno H. J. Ferm. Bioeng. 76 (1993) 33-37
10. Nakamura K., Yamanaka R., Matsuda T., and Harada T. Tetrahedron: Asymmetry 14 (2003) 2659-2681
11. Zhang S., Norrlöw O., Wawrzynczyk J., and Dey E.S. Appl. Environ. Microbiol. 70 (2004) 6776-6782
12. Carnell A.J., Head R., Bassett D., and Schneider M. Tetrahedron: Asymmetry 15 (2004) 821-825
13. Garcia M.J., Rebolledo F., and Gotor V. Tetrahedron: Asymmetry 12 (1992) 1519-1522
14. Fishman A., Eroshov M., Dee-Noor S.S., Mil J., Cogan U., and Effenberger R.. Biotechnol. Bioeng. 74 (2001) 256-263
15. Sugai T., and Ohta H. Agric. Biol. Chem. 53 (1989) 2009-2010
16. Berger B., and Faber K. J. Chem. Soc., Chem. Commun. (1991) 1198-1200
17. Shimizu T., Hiranuma S., and Nakata T. Tetrahedron Lett. 37 (1996) 6145-6148
18. Dijkstra G., Kruizinga W.H., and Kellogg R.M. J. Org. Chem. 52 (1987) 4230-4234
19. Chen C.-S., Fujimoto Y., Girdaukas G., and Sih C.J. J. Am. Chem. Soc. 104 (1982) 7294-7299