Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue.
As an important organic compound, chiral alcohols are the key chiral building blocks to many single enantiomer pharmaceuticals. Asymmetric reduction of the corresponding prochiral ketones to produce the chiral alcohols by biocatalysis is one of the most promising routes. Asymmetric reduction of different kinds of non-natural prochiral ketones catalyzed by various plants tissue was studied in this work. Acetophenone, 4'-chloroacetophenone and ethyl 4-chloroacetoacetate were chosen as the model substrates for simple ketone, halogen-containing aromatic ketone and beta-ketoesters, respectively. Apple (Malus pumila), carrot (Daucus carota), cucumber (Cucumis sativus), onion (Allium cepa), potato (Soanum tuberosum), radish (Raphanus sativus) and sweet potato (Ipomoea batatas) were chosen as the biocatalysts. It was found that these kinds of prochiral ketoness could be reduced by these plants tissue with high enantioselectivity. Both R- and S-form configuration chiral alcohols could be obtained. The e.e. and chemical yield could reach about 98 and 80% respectively for acetophenone and 4'-chloroacetophenone reduction reaction with favorable plant tissue. And the e.e. and yield for ethyl 4-chloroacetoacetate reduction reaction was about 91 and 45% respectively.
College of Chemical Engineering and Technology, Wuhan University of Science and Technology, No. 154 mailbox, 430081, Wuhan, People's Republic of China. yangzju@163.com
Zhong-Hua
ZH
Yang
Rong
R
Zeng
Gai
G
Yang
Yu
Y
Wang
Li-Zhen
LZ
Li
Zao-Sheng
ZS
Lv
Man
M
Yao
Bin
B
Lai
D000438:Alcohols / Q000138:chemical synthesis*; D002384:Catalysis; D005638:Fruit / Q000378:metabolism*; D007659:Ketones / Q000737:chemistry*; D019684:Magnoliopsida / Q000378:metabolism*; D010084:Oxidation-Reduction; D018517:Plant Roots / Q000378:metabolism*
D000438:Alcohols; D007659:Ketones