Kinetic model of asymmetric reduction of 3-oxo-3-phenylpropionic acid ethyl ester using Saccharomyces cerevisiae CGMCC No.2266

Xiaoyan Chen; Zhimin Ou; Guoqing Ying

Korean Journal of Chemical Engineering, Vol.27, No.6, 1841-1846, November, 2010

DOI10.1007/s11814-010-0307-3 Export Citation

Kinetic model of asymmetric reduction of 3-oxo-3-phenylpropionic acid ethyl ester using Saccharomyces cerevisiae CGMCC No.2266

Xiaoyan Chen, Zhimin Ou, and Guoqing Ying^†

Pharmaceuticals College, Zhejiang University of Technology, Hang Zhou, 310014, China

E-mail:

The kinetic model of asymmetric reduction of 3-oxo-3-phenylpropionic acid ethyl ester using Saccharomyces cerevisiae CGMCC No.2266 with 10% glucose as co-substrate to realize the regeneration of NADPH was established. The effect factors on reduction, the type and the content of co-substrate and coenzyme, and the changes of the substrate and product content vs. time during the reaction process were investigated. The results indicate that 10% glucose can increase the reaction conversion from 23.0% to 98.4% and NADPH is reducer. The reduction process conforms with sequence mechanisms. The model parameters are as follows: v(m)=5.0×10^(-4) mol·L^(-1)·h^(-1), k(1)=1.5×10^(-6) mol·L^(-1)·h^(-1), k(2)=3.0×10^(-3) mol·L^(-1)·h^(-1). The kinetic model is in good agreement with the experimental data.

Keywords:Saccharomyces cerevisiae CGMCC No. 2266;Biotransformation;3-Oxo-3-phenylpropionic Acid Ethyl Ester;(S)-3-hydroxy-3-phenylpropionate;Kinetic Model

[References]

Wang PY, Tsai SW, J. Mol. Catal. B: Enzymatic, 59, 70 (2009)
Miles WH, Elizabeth J, Fialcowitz, Halstead ES, Tetrahedron, 57, 9925 (2001)
Hilborn JW, Lu ZH, Jurgens AR, Fang QK, Byers P, Walda SA, Chris H, Tetrahedron Lett., 42, 8919 (2001)
Iliyas SA, Arumugam S, Tetrahedron Letters, 43, 5435 (2002)
He CM, Chang DL, Zhang J, Tetrahedron: Asymmetry, 19, 1347 (2008)
Lapis AAM, Fatima AD, Martins JED, Costab VED, Pillia RA, Tetrahedron Lett., 46, 495 (2005)
Nesterov VV, Kolodiazhnyi OI, Tetrahedron, 63, 6720 (2007)
Matsumae H, Douno H, Yamada S, Nishida T, Ozaki Y, Shibatani T, Tosa T, J. Ferment. Bioeng., 79(1), 28 (1995)
Lou WY, Zong MH, Zhang YY, Wu H, Enzyme Microb. Technol., 35(2-3), 190 (2004)
Li YN, Shi XA, Zong MH, Meng C, Dong YQ, Guo YH, Enzyme Microb. Technol., 40(5), 1305 (2007)
Zeng R, Yang ZH, Yao SJ, Chem. Ind. Eng. Progress, 23, 1169 (2004)
Wang ZL, Xu JH, Wang L, Zhang WZ, Zhuang BH, Qi HS, Enzyme Microb. Technol., 41(3), 296 (2007)
Holland HL, Current Opinion in Chemical Biology, 2, 77 (1998)
Tetsuo T, Kaori A, Nobuaki U, Yukiko T, Hisataka O, Kaoru N, Letter/J. Mol. Catal. B: Enzymatic, 60, 93 (2009)
Yu L, Pei XL, Lei T, Sci. Technol. Food Ind., 5, 100 (2008)
Xiao MT, Huang YY, Meng C, Guo YH, Chin. J. Chem. Eng., 14(1), 73 (2006)
Arinbasarova AY, Karpov AV, Fokina VV, Medentsev AG, Koshcheyenko KA, Enzyme Microb. Technol., 19(7), 501 (1996)
Antonio AR, Sandrine B, Anne GF, Peter JJ, Michele H, J. Biotechnol., 138, 88 (2008)
Bubis M, Zisapel N, Molecular and Cellular Endocrinology, 137, 59 (1998)
Antonella DC, Luca C, Giulio R, Francesca B, Umberto M, Exp. Eye Res., 71, 515 (2000)
Ou Z, Wu J, Yang L, Cen P, Korean J. Chem. Eng., 25(1), 124 (2008)
Rickus JL, Chang PL, Tobin AJ, Zink JI, Dunn B, J. Phys. Chem. B, 108(26), 9325 (2004)

[1] Wang PY, Tsai SW, J. Mol. Catal. B: Enzymatic, 59, 70 (2009)

[2] Miles WH, Elizabeth J, Fialcowitz, Halstead ES, Tetrahedron, 57, 9925 (2001)

[3] Hilborn JW, Lu ZH, Jurgens AR, Fang QK, Byers P, Walda SA, Chris H, Tetrahedron Lett., 42, 8919 (2001)

[4] Iliyas SA, Arumugam S, Tetrahedron Letters, 43, 5435 (2002)

[5] He CM, Chang DL, Zhang J, Tetrahedron: Asymmetry, 19, 1347 (2008)

[6] Lapis AAM, Fatima AD, Martins JED, Costab VED, Pillia RA, Tetrahedron Lett., 46, 495 (2005)

[7] Nesterov VV, Kolodiazhnyi OI, Tetrahedron, 63, 6720 (2007)

[8] Matsumae H, Douno H, Yamada S, Nishida T, Ozaki Y, Shibatani T, Tosa T, J. Ferment. Bioeng., 79(1), 28 (1995)

[9] Lou WY, Zong MH, Zhang YY, Wu H, Enzyme Microb. Technol., 35(2-3), 190 (2004)

[10] Li YN, Shi XA, Zong MH, Meng C, Dong YQ, Guo YH, Enzyme Microb. Technol., 40(5), 1305 (2007)

[11] Zeng R, Yang ZH, Yao SJ, Chem. Ind. Eng. Progress, 23, 1169 (2004)

[12] Wang ZL, Xu JH, Wang L, Zhang WZ, Zhuang BH, Qi HS, Enzyme Microb. Technol., 41(3), 296 (2007)

[13] Holland HL, Current Opinion in Chemical Biology, 2, 77 (1998)

[14] Tetsuo T, Kaori A, Nobuaki U, Yukiko T, Hisataka O, Kaoru N, Letter/J. Mol. Catal. B: Enzymatic, 60, 93 (2009)

[15] Yu L, Pei XL, Lei T, Sci. Technol. Food Ind., 5, 100 (2008)

[16] Xiao MT, Huang YY, Meng C, Guo YH, Chin. J. Chem. Eng., 14(1), 73 (2006)

[17] Arinbasarova AY, Karpov AV, Fokina VV, Medentsev AG, Koshcheyenko KA, Enzyme Microb. Technol., 19(7), 501 (1996)

[18] Antonio AR, Sandrine B, Anne GF, Peter JJ, Michele H, J. Biotechnol., 138, 88 (2008)

[19] Bubis M, Zisapel N, Molecular and Cellular Endocrinology, 137, 59 (1998)

[20] Antonella DC, Luca C, Giulio R, Francesca B, Umberto M, Exp. Eye Res., 71, 515 (2000)

[21] Ou Z, Wu J, Yang L, Cen P, Korean J. Chem. Eng., 25(1), 124 (2008)

[22] Rickus JL, Chang PL, Tobin AJ, Zink JI, Dunn B, J. Phys. Chem. B, 108(26), 9325 (2004)