Asymmetric reduction of 3-oxo-3-phenylpropionic acid ethyl ester by undifferentiated cells of white turnip in phosphate buffer/organic solvent

Zhimin Ou; Qingmei Chen; Gensheng Yang; Li Xu

Korean Journal of Chemical Engineering, Vol.28, No.2, 378-382, February, 2011

DOI10.1007/s11814-010-0353-x Export Citation

Asymmetric reduction of 3-oxo-3-phenylpropionic acid ethyl ester by undifferentiated cells of white turnip in phosphate buffer/organic solvent

Zhimin Ou^†, Qingmei Chen, Gensheng Yang, and Li Xu¹

Pharmaceuticals College, Zhejiang University of Technology, China
¹Pathology Department, Zhejiang Province People’s Hospital, Hang Zhou 310014, China

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Ethyl (S)-3-hydroxy-3-phenylpropionate was synthesized by asymmetric reduction of 3-oxo-3-phenylpropionic acid ethyl ester with undifferentiated cells of white turnip in phosphate buffer/organic solvent. The conversion increased with the LogP(oct) of organic solvent increase. The phosphate buffer (0.2 mol/L, pH 7.0)/dodecane was selected as optimum medium for reduction. The optimal content of dodecane in medium is 10% (v). The conversion decreased with initial substrate concentration increase. Addition of more biomass of plant cells and 10% ethanol as co-substrate can improve conversion. The plant cells can be reused well for three times. The enantiomeric excess of ethyl (S)-3-hydroxy-3-phenylpropionate reached 100% with 1% allyl bromide as inhibitor.

Keywords:Ethyl (S)-3-hydroxy-3-phenylpropionate;Undifferentiated Cells of White Turnip;Phosphate Buffer/Organic Solvent;Asymmetric Reduction

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[1] Engelking H, Pfaller R, Wich G, Weuster-Botz D, Enzyme Microb. Technol., 38(3-4), 536 (2006)

[2] Chenevert R, Fortier G, Rhalid RB, Tetrahedron., 48, 6769 (1992)

[3] Chenevert R, Fortier G, Chem. Lett., 20, 1603 (1991)

[4] Fuller RW, Snoddy HD, Biochem. Pharmacol., 45, 2355 (1993)

[5] Srebrik M, Ramachandran PV, Brown HC, J. Org. Chem., 53, 2916 (1988)

[6] Fuller RW, Perry KW, J. Pharm. Pharmacol., 44, 1041 (1992)

[7] Robertson DW, Krushinski JH, Fuller RW, Leander JD, J. Med. Chem., 31, 1412 (1988)

[8] Scarpi D, Occhiato EG, Guarna A, Tetrahedron: Asymmetry., 16, 1479 (2005)

[9] Maczka WK, Mironowicz A, Tetrahedron: Asymmetry., 15, 1965 (2004)

[10] Andrade LH, Utsunomiya RS, Omori AT, Porto ALM, Comasseto JV, J. Mol. Catal. B: Enzym., 38, 84 (2006)

[11] Itoh K, Sakamaki H, Nakamura K, Horiuchi A, Tetrahedron: Asymmetry., 16, 1403 (2005)

[12] Chai W, Hiroki H, Jumpei S, Horiuchi CA, Phytochem., 57, 669 (2001)

[13] Bruni R, Fantin G, Maietti S, Medici A, Pedrini P, Sacchetti G, Tetrahedron: Asymmetry., 17, 2287 (2006)

[14] Hamada H, Miyamoto Y, Nakajima N, Furuya T, J. Mol. Catal.B: Enzym., 5, 187 (1998)

[15] Hernandez L, Luna H, Solis A, Vazquez A, Tetrahedron: Asymmetry., 17, 2813 (2006)

[16] Solis A, Luna H, Perez HI, Manjarrez N, Tetrahedron: Asymmetry., 14, 2351 (2003)

[17] Hamada H, Yasumune H, Fuchikami Y, Hirata T, Sattler I, Williams HJ, Ian Scott A, Phytochem., 44, 615 (1997)

[18] Hegazy MF, Chika K, Akihito M, Ahmed AA, Hirata T, J.Mol. Catal. B: Enzym., 39, 13 (2006)

[19] Ushio K, Hada J, Tanaka Y, Ebara K, Enzyme Microb. Technol., 15, 222 (1993)