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

Yasuaki Fukuyama; Kaori Matoishi; Masakazu Iwasaki; Eiji Takizawa; Mamoru Miyazaki; Hiromichi Ohta; Satoshi Hanzawa; Hitoshi Kakidani; Takeshi Sugai

doi:10.1271/bbb.63.1664

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

Yasuaki Fukuyama, Kaori Matoishi, Masakazu Iwasaki, Eiji Takizawa, Mamoru Miyazaki, Hiromichi Ohta, Satoshi Hanzawa, Hitoshi Kakidani, Takeshi Sugai

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1664-1666
Number of pages	3
Journal	Bioscience, Biotechnology and Biochemistry
Volume	63
Issue number	9
DOIs	https://doi.org/10.1271/bbb.63.1664
Publication status	Published - 1999 Jan 1

Keywords

(R)-α-fluorophenylacetic acid
Arylmalonate decarboxylase
Asymmetric decarboxylation
α-fluorophenylmalonic acid

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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title = "Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid",

abstract = "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.",

keywords = "(R)-α-fluorophenylacetic acid, Arylmalonate decarboxylase, Asymmetric decarboxylation, α-fluorophenylmalonic acid",

author = "Yasuaki Fukuyama and Kaori Matoishi and Masakazu Iwasaki and Eiji Takizawa and Mamoru Miyazaki and Hiromichi Ohta and Satoshi Hanzawa and Hitoshi Kakidani and Takeshi Sugai",

year = "1999",

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doi = "10.1271/bbb.63.1664",

language = "English",

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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

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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 -

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

Abstract

Keywords

ASJC Scopus subject areas

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