Enzymatic synthesis of α-arbutin by α-anomer-selective glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701

Jun Kurosu, Toshiyuki Sato, Keishiro Yoshida, Takanori Tsugane, Susumu Shimura, Kohtaro Kirimura, Kuniki Kino, Shoji Usami

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

α-Arbutin, a useful cosmetic ingredient, was selectively synthesized by α-anomer-selective glucosylation of hydroquinone with maltose as a glucosyl donor using lyophilized cells of Xanthomonas campestris WU-9701 as a biocatalyst. When 45 mM hydroquinone and 120 mg of lyophilized cells showing 11 nkat of α-glucosyl transfer activity were shaken in 2 ml of 10 mM H3BO3-NaOH-KCl buffer (pH 7.5) containing 1.2 M maltose at 40°C, only one form of hydroquinone glucoside was selectively obtained as a product and identified as hydroquinone 1-O-α-D-glucopyranoside (α-arbutin) by 13C-NMR, 1H-NMR and two-dimensional HMBC analysis. Although hydroquinone has two phenolic -OH groups at the para position in its structure, only one -OH group, but not both -OHs, was glucosylated and no other glucosylated products such as maltotriose were detected in the reaction mixture. The reaction at 40°C for 36 h under optimum conditions yielded 42 mM α-arbutin, and the maximum molar conversion yield based on the amount of hydroquinone supplied reached 93%.

Original languageEnglish
Pages (from-to)328-330
Number of pages3
JournalJournal of Bioscience and Bioengineering
Volume93
Issue number3
DOIs
Publication statusPublished - 2002 Jan 1

Keywords

  • Hydroquinone
  • Transglucosylation
  • Xanthomonas campestris
  • α-anomer-selective glucosylation
  • α-arbutin

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology

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