Lipase-catalyzed hydrolytic resolution of (R,S)-3-hydroxy-3-phenylpropionates in biphasic media

Journal of the Taiwan Institute of Chemical Engineers

Volumn 42, Issue 3, 2011, Pages 408-412

  Cho, Shu Hhin ^a   Wang, Pei Yun ^a   Tsai, Shau Wei ^a  

^a CHANG GUNG UNIVERSITY   (Taiwan)

Author keywords

(R,S) 3 Hydroxy 3 phenylpropionates; Covalent immobilization; Hydrolytic resolution; Lipase PS

Indexed keywords

(R,S)-3-HYDROXY-3-PHENYLPROPIONATES; BIPHASIC; COVALENT IMMOBILIZATION; ENZYME PREPARATION; HYDROLYTIC RESOLUTION; KINETIC ANALYSIS; KINETIC CONSTANT; LIPASE-CATALYZED; MAIN EFFECT; OPTIMAL REACTION CONDITION; ORGANIC PHASE; PSEUDOMONAS CEPACIA; SEPABEADS;

ENANTIOSELECTIVITY; METHANOL; PARAFFINS; RATE CONSTANTS;

ENZYME IMMOBILIZATION;

EID: 79958229337     PISSN: 18761070     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jtice.2010.09.005     Document Type: Article

References (18)

1. Boaz N.W. Enzymatic Hydrolysis of Ethyl 3-Hydroxy-3-phenylpropanoate: Observations on an Enzyme Active-Site Model. J. Org. Chem. 1992, 57:4289.
2. Bornscheuer U.T., Herar A., Kreye L., Wendel V., Capewell A., Meyer H.H., Scheper T., Kolisis F.N. Factors Affecting the Lipase Catalyzed Transesterification Reactions of 3-Hydroxy Esters in Organic Solvents. Tetrahedron: Asymm. 1993, 4:1007.
3. Guaragna A., Nisco M.D., Pedatella S., Palumbo G. Studies Towards Lipid A: A Synthetic Strategy for the Enantioselective Preparation of 3-Hydroxy Fatty Acids. Tetrahedron: Asymm. 2006, 17:2839.
4. Hoff B.H., Anthonsen T. Lipase-catalyzed Resolution of Esters of 4-Chloro-3-Hydroxybutanoic Acid: Effects of the Alkoxy Group and Solvent on the Enantiomeric Ratio. Tetrahedron: Asymm. 1999, 10:1401.
5. Hu B., Prashad M., Har D., Prasad K., Repic O., Blacklock T.J. An Efficient Synthesis of (R)-2-Butyl-3-Hydroxypropionic Acid. Org. Process Res. Dev. 2007, 11:564.
6. Huerta F.F., Backvall J.-E. Enantioselective Synthesis of β-Hydroxy Acid Derivatives via a One-pot Aldol Reaction-Dynamic Kinetic Resolution. Org. Lett. 2001, 3:1209.
7. Kaga H., Hirosawa K., Takahashi T., Goto K. Lipase Catalyzed Transesterification of 2-Substituted 3-Hydroxy esters. Chirality 1998, 10:693.
8. Nascimento M.G., Zanotto S.P., Melegari S.P., Fernandes L., Sa M.M. Resolution of α-Methylene-β-Hydroxy Esters Catalyzed by Free and Immobilized Pseudomonas sp. Lipase. Tetrahedron: Asymm. 2003, 14:3111.
9. Padhi S.K., Titu D., Pandian N.G., Chadha A. Deracemisation of β-Hydroxy Esters Using Immobilised Whole Cells of Candida parapsilosis ATCC 7330: Substrate Specificity and Mechanistic Investigation. Tetrahedron 2006, 62:5133.
10. Ribeiro C.M.R., Passaroto E.N., Eugenia C.S.B. Ultrasound in Enzymatic Resolution of Ethyl 3-Hydroxy-3-Phenylpropanoate. Tetrahedron Lett. 2001, 42:6477.
11. Spengler J., Albericio F. Asymmetric Synthesis of α-Unsubstituted β-Hydroxy Acids. Curr. Org. Syn. 2008, 5:151.
12. Wang P.Y., Chen T.L., Tsai S.W., Kroutil W. Hydrolytic Resolution of (R,S)-2-Hydroxycarboxylic Acid Esters in Biphasic Media: Implication for Rate-limiting Formation or Breakdown of Tetrahedral Intermediates in Acylation Step. Biotechnol. Bioeng. 2007, 98:30.
13. Wang P.Y., Chen T.L., Tsai S.W. Hydrolytic Resolution of (R,S)-3-Hydroxy-3-Phenylpropionates by Esterase from Klebsiella oxytoca: Effects of Leaving Alcohol, Covalent Immobilization and Aqueous pH. J. Mol. Cat. B: Enzym. 2009, 59:70.
14. Wang P.Y., Tsai S.W. Hydrolytic Resolution of (R,S)-Ethyl Mandelate in Biphasic Media via Klebsiella oxytoca Hydrolase. Enzyme Microb. Technol. 2005, 37:266.
15. Wang P.Y., Tsai S.W., Chen T.L. Improvement of Enantioselectivity and Stability of Klebsiella oxytoca Hydrolase Immobilized on Eupergit C 250L. J. Chem. Technol. Biotechnol. 2008, 83:1518.
16. Wang P.Y., Tsai S.W., Chen T.L. Improvements of Enzyme Activity and Enantioselectivity via Combined Substrate Engineering and Covalent Immobilization. Biotechnol. Bioeng. 2008, 101:460.
17. Wang P.Y., Tsai S.W. Modification of Enzyme Surface Negative Charges via Covalent Immobilization for Tailoring the Activity and Enantioselectivity. J. Taiwan Inst. Chem. Engrs. 2009, 40:364.
18. Xu C., Yuan C. Candida Rugosa Lipase-Catalyzed Kinetic Resolution of β-Hydroxy-β-Arylpropionates and δ-Hydroxy-δ-Aryl-β-Oxo-Pentanoates. Tetrahedron 2005, 61:2169.