TY - JOUR
T1 - Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid
AU - Fukuyama, Yasuaki
AU - Matoishi, Kaori
AU - Iwasaki, Masakazu
AU - Takizawa, Eiji
AU - Miyazaki, Mamoru
AU - Ohta, Hiromichi
AU - Hanzawa, Satoshi
AU - Kakidani, Hitoshi
AU - Sugai, Takeshi
PY - 1999/1/1
Y1 - 1999/1/1
N2 - A preparative-scale asymmetric synthesis of (R)-α-fluorophenylacetic acid, a useful chiral derivatizing reagent, is described. Starting from ethyl α-bromophenylacetate, α-fluorophenylmalonic acid dipotassium 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)-α-flurophenylacetic acid (>99% e.e.) was prepared in a quantitative yield.
AB - A preparative-scale asymmetric synthesis of (R)-α-fluorophenylacetic acid, a useful chiral derivatizing reagent, is described. Starting from ethyl α-bromophenylacetate, α-fluorophenylmalonic acid dipotassium 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)-α-flurophenylacetic acid (>99% e.e.) was prepared in a quantitative yield.
KW - (R)-α-fluorophenylacetic acid
KW - Arylmalonate decarboxylase
KW - Asymmetric decarboxylation
KW - α-fluorophenylmalonic acid
UR - http://www.scopus.com/inward/record.url?scp=0001211797&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0001211797&partnerID=8YFLogxK
U2 - 10.1271/bbb.63.1664
DO - 10.1271/bbb.63.1664
M3 - Article
AN - SCOPUS:0001211797
SN - 0916-8451
VL - 63
SP - 1664
EP - 1666
JO - Bioscience, Biotechnology and Biochemistry
JF - Bioscience, Biotechnology and Biochemistry
IS - 9
ER -