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

13 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
DOIs
Publication statusPublished - 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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  • Cite this

    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, 63(9), 1664-1666. https://doi.org/10.1271/bbb.63.1664