Biocatalytic kinetic resolution of rac-1-phenylethanol and rac-2-pentanol in hexane medium: Acyl donorand water content effects

Canadian Journal of Chemical Engineering

Volumn 88, Issue 3, 2010, Pages 442-446

  de los Ros A P ^a   Hernandez Fernandez F J ^a   Tomas Alonso F ^b   Gomez D ^b   Vllora G ^b  

^a TECHNICAL UNIVERSITY OF CARTAGENA   (Spain)

^b UNIVERSITY OF MURCIA   (Spain)

Author keywords

2 pentanol; Biocatalysis; Kinetic resolution; Lipase; Rac phenylethanol

Indexed keywords

1-PHENYLETHANOL; 2-PENTANOL; ACYL DONORS; BIOCATALYSIS; BUTYL BUTYRATE; CANDIDA ANTARCTICA LIPASE B; HIGH ENANTIOSELECTIVITY; KINETIC RESOLUTION; PHENYLETHANOL; VINYL ESTERS;

ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; ENZYMES; ESTERS; HEXANE; WATER CONTENT;

ETHANOL;

EID: 77953333062     PISSN: 00084034     EISSN: 1939019X     Source Type: Journal    
DOI: 10.1002/cjce.20285     Document Type: Article

References (16)

1. Arïens, E.J., "Stereochemistry: A Source of Problems in Medicinal Chemistry," Med.R es.R ev. 6, 451-466 (1986).
2. Audia, J.E., T.C. Britton, J.J. Droste, B.K. Folmer, G.W. Huffman, V. John, L.H. Latimer, T.E. Mabry, J.S. Nissen, W.J. Porter, J.K. Reel, E.D. Thorsett, J.S. Tung, J. Wu, C.N. Eid and W.L. Scott, Patent WO 98/22494.(1998).
3. Berglund, P., "Controlling Lipase Enantioselectivity for Organic Synthesis," Biomol.Eng. 18, 13-22 (2001).
4. Bornscheuer, U.T.and R.J.Kazlauskas, "Hydrolases in Organic Syntheses Regio- and Stereoselective Biotransformations," Wiley-VCH, Weinheim (1999).
5. Ćardenas, F., M.S. De Castro, J.M. Śanchez-Montero, J.V. Sinisterra, M. Balmaceda, S.W. Elson and E. Alvarez, "Novel Microbial Lipases: Catalytic Activity in Reactions in Organic Media," Enzyme Microb.T echnol. 28, 145-154 (2001).
6. Chua, L.S.and M.R. Sarmidi, "Immobilised Lipase-Catalysed Resolution of (R,S)-1-Phenylethanol in Recirculated Packed Bed Reactor," J.Mol.Catal.B Enzym. 28, 111-119 (2004).
7. Ivanov, A.E.and M.P. Schneider, "Methods for the Immobilization of Lipases and Their Use for Ester Synthesis," J.Mol.Catal.B Enzym. 3, 303-309 (1997).
8. Jecfa www.fao.org/ag/agn/jecfa-flav/search.html?lang=en (accessed November 15, 2007).(2007).
9. Maier, N.M., P.F ranco and W. Lindner, "Separation of Enantiomers: Needs, Challenges, Perspectives," J. Chromatogr.A 906, 3-33 (2001).
10. Messiano, A.J., E.J. Beckman and A.J. Russell, "Supercritical Biocatalysis," Chem.R ev. 99, 623-633 (1999).
11. N̈oel, M., P. Lozano, M. Vaultier and J.L. Iborra, "Kinetic Resolution for Rac-2-Pentanol Catalyzed by Candida Antarctica Lipase B in the Ionic Liquid, 1-Butyl-3-Methylimidazolium Bis[(Trifluoromethyl)Sulfonyl] Amide," Biotechnol.Lett. 26, 301-306 (2004).
12. Scḧofer, S.H., N. Kaftzik, P. Wasserscheid and U. Kragl, "Enzyme Catalysis in Ionic Liquids: Lipase Catalysed Kinetic Resolution of 1-Phenylethanol With Improved Enantioselectivity," Chem.Commun. 5, 425-426 (2001).
13. Suan, C.L.and M.R. Sarmidi, "Immobilised Lipase-Catalysed Resolution of (R,S)-1-Phenylethanol in Recirculated Packed Bed Reactor," J.Mol.Catal.B Enzym. 28, 111-119 (2004).
14. Suginaka, K., Y.Ha yashi and Y.Y amamoto, "Highly Selective Resolution of Secondary Alcohols and Acetoacetates With Lipases and Diketene in Organic Media," Tetrahedron: Asymmetry 7, 1153-1158 (1996).
15. Wainer, I.W., "Drug Stereochemistry," In: "Analytical Methods and Pharmacology," Irving W. Wainer (Ed.) 2nd ed., Marcel Dekker, New York (1993).
16. Ward, T.J.and B.A. Baker, "Chiral Separations," Anal.Chem. 80, 4363-4372 (2008)