Asymmetric reduction of chloroacetophenones to produce chiral alcohols with microorganisms
Tóm tắt
Four strains of yeast with reduction activity of chloroacetophenones were screened, in which Saccharomyces cerevisiae B5 showed best reduction activity and stereoselectivity. High optical purity (R)-2′-chloro-1-phenylethanol can be obtained with Saccharomyces cerevisiae B5 as biocatalyst. The influence of several co-substrates on the enantiometric excess (ee%) and yield of (R)-2′-chloro-1-phenylethanol was evaluated. 5% (v/v) ethanol is optimal cosubstrate for (R)-2′-chloro-1-phenylethanol formation. The optimal bioconversion conditions of 2′-chloroacetophenone catalyzed by Saccharomyces cerevisiae B5 are as follows: pH 8.0, 25 °C and 24 h. The yield and the enantiometric excess of (R)-2′-chloro-1-phenylethanol can both reach more than 99% with 10.75 g/l Saccharomyces cerevisiae B5 (the cell dry weight) and 1 g/l 2′-chloroacetophenone used in the biotransformation.
Tài liệu tham khảo
H. Jun-Yao, S. Zhi-hao, R. Wen-Quan and X. Yan, Proc. Biochem., 41, 244 (2006).
R. Chenevert and G. Fortier, Chem. Lett., 9, 1603 (1991).
Z. Konsoula and M. Liakopoulou-Kyriakides, Enzyme Microb. Technol., 39, 690 (2006).
K. P. Santosh and C. Anju, Tetrahedron: Asymm., 16, 2790 (2005).
H. Hioki, T. Hashimoto and M. Kodama, Tetrahedron: Asymm., 11, 829 (2000).
M. S. M. Humberto, D. F. M. Cíntia, J. S. M. Paulo, H. A. S. Maria and R. R. J. Augusto, Enzyme Microb. Technol., 37, 121 (2005).
J. D. Stewart, Curr. Opin. Biotech., 11, 363 (2000).
A. C. Dahl, M. Fjeldberg and J. O. Madsen, Tetrahedron: Asymm., 10, 551 (1999).
H. Yang, A. Jonsson and E. Wehtje, BBA — General Subjects, 1336, 51 (1997).
T. Suzuki, H. Idogaki and N. Kasai, Enzyme Microb. Technol., 24, 13 (1999).
P. Davoli, A. Forni and I. Moretti, Enzyme Microb. Technol., 25, 149 (1999).
L.Y. Zheng and Y. L. Xiao, Korean J. Chem. Eng., 21, 201 (2004).
A. C. Dahl, M. Fjeldberg and J. O. Madsen, Tetrahedron: Asymm., 9, 4395 (1998).
J. Shim, G.-Y. Kim, K.-H. Yeon, S.-H. Cho, J.-J. Woo and S.-H. Moon, Korean J. Chem. Eng., 24, 72 (2007).
J. R. Wendhausen and P. J. S. Moran, J. Mol. Catal. B: Enzym., 5, 69 (1998).
K. Nakamura, Y. Kawai and A. Ohno, Tetrahedron Lett., 31, 267 (1990).
B. Abdelbaki and K. A. Mohamed, Korean J. Chem. Eng., 24, 16 (2007).
S. Shimizu, M. Kataoka and M. Katoh, Appl. Environ. Microbiol., 56, 2374 (1990).