α-Anomer-selective glucosylation of (+)-catechin by the crude enzyme, showing glucosyl transfer activity, of Xanthomonas campestris WU-9701

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

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47 Citations (Scopus)

Abstract

α-Anomer-selective glucosylation of (+)-catechin was carried out using the crude enzyme, showing α-glucose transferring activity, of Xanthomonas campestris WU-9701 with maltose as a glucosyl donor. When 60 mg of (+)-catechin and 50 mg of the enzyme (5.25 units as maltose hydrolysing activity) were incubated in 10 ml of 10 mM citrate-Na2HPO4 buffer (pH 6.5) containing 1.2 M maltose at 45°C, only one (+)-catechin glucoside was selectively obtained as a product. The (+)-catechin glucoside was identified as (+)-catechin 3′-O-α-D-glucopyranoside (α-C-G) by 13C-NMR, 1H-NMR and two-dimensional HMBC analysis. The reaction at 45°C for 36 h under the optimum conditions gave 12 mM α-C-G, 5.4 mg/ml in the reaction mixture, and the maximum molar conversion yield based on the amount of (+)-catechin supplied reached 57.1%. At 20°C, the solubility in pure water of α-C-G, of 450 mg/ml, was approximately 100 fold higher than that of (+)-catechin, of 4.6 mg/ml. Since α-C-G has no bitter taste and a slight sweet taste compared with (+)-catechin which has a very bitter taste, α-C-G may be a desirable additive for foods, particularly sweet foods.

Original languageEnglish
Pages (from-to)625-630
Number of pages6
JournalJournal of Bioscience and Bioengineering
Volume90
Issue number6
DOIs
Publication statusPublished - 2000 Jan 1

Keywords

  • (+)-catechin
  • Anomer-selective glucosylation
  • Glucoside
  • Transglucosylation
  • Xanthomonas campestris

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Applied Microbiology and Biotechnology

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