Selective α-glucosylation of eugenol by α-glucosyl transfer enzyme of Xanthomonas campestris WU-9701

Toshiyuki Sato, Hiroaki Takeuchi, Kei Takahashi, Jun Kurosu, Keishiro Yoshida, Takanori Tsugane, Susumu Shimura, Kuniki Kino, Kohtaro Kirimura

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

For one-step enzymatic synthesis of eugenyl α-glucoside as a promising pro-drug for a hair restorer and a derivative of spices, selective α-glucosylation of eugenol was carried out using the α-glucosyl transfer enzyme of Xanthomonas campestris WU-9701. When 130 μmol eugenol and crude enzyme showing 1.0 unit of α-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3-NaOH-KCl buffer (pH 8.0) containing 1.2 M maltose as a glucosyl donor at 40°C, only one form of eugenyl glucoside was selectively obtained as a product and identified as eugenyl α-D-glucopyranoside (α-EG) by 13C-NMR, 1H-NMR, and two-dimensional heteronuclear multiple-bond coherence analyses. In the reaction, no other glucosylated products such as maltotriose or eugenyl maltoside were detected in the reaction mixture. The reaction at 40°C for 48 h under the above conditions yielded 68 μmol α-EG in 2 ml suspension, and the maximum molar conversion yield based on the amount of eugenol supplied reached 52%.

Original languageEnglish
Pages (from-to)199-202
Number of pages4
JournalJournal of Bioscience and Bioengineering
Volume96
Issue number2
DOIs
Publication statusPublished - 2003 Jan 1

Keywords

  • Eugenol
  • Pro-drug
  • Selective α-glucosylation
  • Transglucosylation
  • Xanthomonas campestris

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology

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