TY - JOUR
T1 - Asymmetric reduction of ketones using recombinant E. coli cells that produce a versatile carbonyl reductase with high enantioselectivity and broad substrate specificity
AU - Ema, Tadashi
AU - Yagasaki, Hideo
AU - Okita, Nobuyasu
AU - Takeda, Masahiro
AU - Sakai, Takashi
N1 - Funding Information:
We thank Dr. Hiroaki Yamamoto (Daicel Chemical Industries) and Professor Tetsuo Toraya (Okayama University) for the determination of the internal amino-acid sequences of SCR and useful advice on gene expression, respectively. This work was supported by a Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science (JSPS) and by a grant from Venture Business Laboratory of Okayama University. We are grateful to the SC-NMR Laboratory of Okayama University for the measurement of NMR spectra.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2006/6/26
Y1 - 2006/6/26
N2 - The gene encoding a versatile biocatalyst that shows high enantioselectivity for a variety of ketones, SCR (Saccharomyces cerevisiae carbonyl reductase), has been identified, cloned, and expressed in Escherichia coli. Two types of expression systems with high NADPH-regenerating capacities have been constructed. One is the tandem system, where the genes encoding SCR and GDH (glucose dehydrogenase) are located in the same plasmid, and the other is the two-plasmid system, where each of the SCR and GDH genes is located in separate plasmids that can coexist in one E. coli cell. Asymmetric reduction of ketones with the recombinant E. coli cells gave synthetically useful 20 alcohols, 11 of which were enantiomerically pure. The productivity of one of these products was as high as 41 g/L.
AB - The gene encoding a versatile biocatalyst that shows high enantioselectivity for a variety of ketones, SCR (Saccharomyces cerevisiae carbonyl reductase), has been identified, cloned, and expressed in Escherichia coli. Two types of expression systems with high NADPH-regenerating capacities have been constructed. One is the tandem system, where the genes encoding SCR and GDH (glucose dehydrogenase) are located in the same plasmid, and the other is the two-plasmid system, where each of the SCR and GDH genes is located in separate plasmids that can coexist in one E. coli cell. Asymmetric reduction of ketones with the recombinant E. coli cells gave synthetically useful 20 alcohols, 11 of which were enantiomerically pure. The productivity of one of these products was as high as 41 g/L.
KW - Alcohol
KW - Asymmetric synthesis
KW - Biotransformation
KW - Reduction
UR - http://www.scopus.com/inward/record.url?scp=33646758223&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33646758223&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2006.04.061
DO - 10.1016/j.tet.2006.04.061
M3 - Article
AN - SCOPUS:33646758223
VL - 62
SP - 6143
EP - 6149
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 26
ER -