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

Research output: Contribution to journalArticle

12 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 languageEnglish
Pages (from-to)1664-1666
Number of pages3
JournalBioscience, Biotechnology and Biochemistry
Volume63
Issue number9
Publication statusPublished - 1999 Sep

Fingerprint

Acids
synthesis
acids
Enzymes
enzymes
Fluorides
Escherichia coli
Substitution reactions
Salts
Ions
fluorides
Substrates
ions
salts
2-(4-fluorophenyl)acetic acid
malonate decarboxylase

Keywords

  • α-fluorophenylmalonic acid
  • (r)-α-fluorophenylacetic acid
  • Arylmalonate decarboxylase
  • Asymmetric decarboxylation

ASJC Scopus subject areas

  • Food Science
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biotechnology
  • Chemistry (miscellaneous)
  • Applied Microbiology and Biotechnology

Cite this

Fukuyama, Y., Matoishi, K., Iwasaki, M., Takizawa, E., Miyazaki, M., Ohta, H., ... Sugai, T. (1999). Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid. Bioscience, Biotechnology and Biochemistry, 63(9), 1664-1666.

Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid. / Fukuyama, Yasuaki; Matoishi, Kaori; Iwasaki, Masakazu; Takizawa, Eiji; Miyazaki, Mamoru; Ohta, Hiromichi; Hanzawa, Satoshi; Kakidani, Hitoshi; Sugai, Takeshi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 63, No. 9, 09.1999, p. 1664-1666.

Research output: Contribution to journalArticle

Fukuyama, Y, Matoishi, K, Iwasaki, M, Takizawa, E, Miyazaki, M, Ohta, H, Hanzawa, S, Kakidani, H & Sugai, T 1999, 'Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid', Bioscience, Biotechnology and Biochemistry, vol. 63, no. 9, pp. 1664-1666.
Fukuyama Y, Matoishi K, Iwasaki M, Takizawa E, Miyazaki M, Ohta H et al. Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid. Bioscience, Biotechnology and Biochemistry. 1999 Sep;63(9):1664-1666.
Fukuyama, Yasuaki ; Matoishi, Kaori ; Iwasaki, Masakazu ; Takizawa, Eiji ; Miyazaki, Mamoru ; Ohta, Hiromichi ; Hanzawa, Satoshi ; Kakidani, Hitoshi ; Sugai, Takeshi. / Preparative-scale enzyme-catalyzed synthesis of (R)-α-fluorophenylacetic acid. In: Bioscience, Biotechnology and Biochemistry. 1999 ; Vol. 63, No. 9. pp. 1664-1666.
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