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Received April 14, 2010
Accepted June 10, 2010
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Asymmetric reduction of 3-oxo-3-phenylpropionic acid ethyl ester by undifferentiated cells of white turnip in phosphate buffer/organic solvent
Pharmaceuticals College, Zhejiang University of Technology, China 1Pathology Department, Zhejiang Province People’s Hospital, Hang Zhou 310014, China
oozzmm@163.com
Korean Journal of Chemical Engineering, February 2011, 28(2), 378-382(5)
https://doi.org/10.1007/s11814-010-0353-x
https://doi.org/10.1007/s11814-010-0353-x
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Abstract
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.
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References
Engelking H, Pfaller R, Wich G, Weuster-Botz D, Enzyme Microb. Technol., 38(3-4), 536 (2006)
Chenevert R, Fortier G, Rhalid RB, Tetrahedron., 48, 6769 (1992)
Chenevert R, Fortier G, Chem. Lett., 20, 1603 (1991)
Fuller RW, Snoddy HD, Biochem. Pharmacol., 45, 2355 (1993)
Srebrik M, Ramachandran PV, Brown HC, J. Org. Chem., 53, 2916 (1988)
Fuller RW, Perry KW, J. Pharm. Pharmacol., 44, 1041 (1992)
Robertson DW, Krushinski JH, Fuller RW, Leander JD, J. Med. Chem., 31, 1412 (1988)
Scarpi D, Occhiato EG, Guarna A, Tetrahedron: Asymmetry., 16, 1479 (2005)
Maczka WK, Mironowicz A, Tetrahedron: Asymmetry., 15, 1965 (2004)
Andrade LH, Utsunomiya RS, Omori AT, Porto ALM, Comasseto JV, J. Mol. Catal. B: Enzym., 38, 84 (2006)
Itoh K, Sakamaki H, Nakamura K, Horiuchi A, Tetrahedron: Asymmetry., 16, 1403 (2005)
Chai W, Hiroki H, Jumpei S, Horiuchi CA, Phytochem., 57, 669 (2001)
Bruni R, Fantin G, Maietti S, Medici A, Pedrini P, Sacchetti G, Tetrahedron: Asymmetry., 17, 2287 (2006)
Hamada H, Miyamoto Y, Nakajima N, Furuya T, J. Mol. Catal.B: Enzym., 5, 187 (1998)
Hernandez L, Luna H, Solis A, Vazquez A, Tetrahedron: Asymmetry., 17, 2813 (2006)
Solis A, Luna H, Perez HI, Manjarrez N, Tetrahedron: Asymmetry., 14, 2351 (2003)
Hamada H, Yasumune H, Fuchikami Y, Hirata T, Sattler I, Williams HJ, Ian Scott A, Phytochem., 44, 615 (1997)
Hegazy MF, Chika K, Akihito M, Ahmed AA, Hirata T, J.Mol. Catal. B: Enzym., 39, 13 (2006)
Ushio K, Hada J, Tanaka Y, Ebara K, Enzyme Microb. Technol., 15, 222 (1993)
Chenevert R, Fortier G, Rhalid RB, Tetrahedron., 48, 6769 (1992)
Chenevert R, Fortier G, Chem. Lett., 20, 1603 (1991)
Fuller RW, Snoddy HD, Biochem. Pharmacol., 45, 2355 (1993)
Srebrik M, Ramachandran PV, Brown HC, J. Org. Chem., 53, 2916 (1988)
Fuller RW, Perry KW, J. Pharm. Pharmacol., 44, 1041 (1992)
Robertson DW, Krushinski JH, Fuller RW, Leander JD, J. Med. Chem., 31, 1412 (1988)
Scarpi D, Occhiato EG, Guarna A, Tetrahedron: Asymmetry., 16, 1479 (2005)
Maczka WK, Mironowicz A, Tetrahedron: Asymmetry., 15, 1965 (2004)
Andrade LH, Utsunomiya RS, Omori AT, Porto ALM, Comasseto JV, J. Mol. Catal. B: Enzym., 38, 84 (2006)
Itoh K, Sakamaki H, Nakamura K, Horiuchi A, Tetrahedron: Asymmetry., 16, 1403 (2005)
Chai W, Hiroki H, Jumpei S, Horiuchi CA, Phytochem., 57, 669 (2001)
Bruni R, Fantin G, Maietti S, Medici A, Pedrini P, Sacchetti G, Tetrahedron: Asymmetry., 17, 2287 (2006)
Hamada H, Miyamoto Y, Nakajima N, Furuya T, J. Mol. Catal.B: Enzym., 5, 187 (1998)
Hernandez L, Luna H, Solis A, Vazquez A, Tetrahedron: Asymmetry., 17, 2813 (2006)
Solis A, Luna H, Perez HI, Manjarrez N, Tetrahedron: Asymmetry., 14, 2351 (2003)
Hamada H, Yasumune H, Fuchikami Y, Hirata T, Sattler I, Williams HJ, Ian Scott A, Phytochem., 44, 615 (1997)
Hegazy MF, Chika K, Akihito M, Ahmed AA, Hirata T, J.Mol. Catal. B: Enzym., 39, 13 (2006)
Ushio K, Hada J, Tanaka Y, Ebara K, Enzyme Microb. Technol., 15, 222 (1993)
