Enzymatic carboxylation of hydroxystilbenes by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions

Masaru Sato, Nozomu Sakurai, Hideyuki Suzuki, Daisuke Shibata, Kuniki Kino

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We examined 66 aromatics for carboxylation by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions. The enzyme carboxylated resorcinol, catechol, 5-methylresorcinol and three hydroxystilbenes (resveratrol, gnetol, and piceatannol) with high yields. Except for catechol, the structures of these substrates include a 1,3-dihydroxybenzene moiety. Other compounds gave no reaction products. The reaction products from resveratrol and gnetol were 2,6-dihydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoic acid and 2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid, respectively, as determined by mass spectrometry and nuclear magnetic resonance analyses. Kinetic analyses of the carboxylation reactions indicated that resveratrol and gnetol are better substrates than resorcinol or catechol.

Original languageEnglish
Pages (from-to)348-352
Number of pages5
JournalJournal of Molecular Catalysis B: Enzymatic
Volume122
DOIs
Publication statusPublished - 2015 Dec 1

Keywords

  • Enzymatic carboxylation
  • Gnetol
  • Hydroxystilbene
  • Resveratrol
  • γ-Resorcylic acid decarboxylase

ASJC Scopus subject areas

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

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