Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid

被引:10
作者
Fukuyama, Y
Matoishi, K
Iwasaki, M
Takizawa, E
Miyazaki, M
Ohta, H
Hanzawa, S
Kakidani, H
Sugai, T
机构
[1] Keio Univ, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
[2] Tosoh Corp, Tokyo Res Ctr, Ayase, Kanagawa 2521123, Japan
关键词
(R)-alpha-fluorophenylacetic acid; arylmalonate decarboxylase; alpha-fluorophenylmalonic acid; asymmetric decarboxylation;
D O I
10.1271/bbb.63.1664
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A preparative-scale asymmetric synthesis of (R)-alpha-fluorophenylacetic acid, a useful chiral derivatizing reagent, is described. Starting from ethyl alpha-bromophenylacetate, alpha-fluorophenylmalonic acid dipotassinm salt was prepared in three steps (54% yield), including nucleophilic substitution by the fluoride ion as the keystep. Both the purified form and crude preparation of arylmalonate decarboxylase in E. coli worked well on this substrate, and (R)-alpha-flurophenylacetic acid (>99% e.e.) was prepared in a quantitative yield.
引用
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页码:1664 / 1666
页数:3
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