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, Kotaro Kirimura, Kuniki Kino, Shoji Usami

    Research output: Contribution to journalArticle

    45 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

    Fingerprint

    Xanthomonas campestris
    Maltose
    Catechin
    Enzymes
    Nuclear magnetic resonance
    Glucose
    Glucosides
    Solubility
    Dilatation and Curettage
    Food Additives
    Water
    Citric Acid
    Buffers
    Food

    Keywords

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

    ASJC Scopus subject areas

    • Biotechnology
    • Bioengineering

    Cite this

    α-Anomer-selective glucosylation of (+)-catechin by the crude enzyme, showing glucosyl transfer activity, of Xanthomonas campestris WU-9701. / Sato, Toshiyuki; Nakagawa, Hiroyuki; Kurosu, Jun; Yoshida, Keishiro; Tsugane, Takanori; Shimura, Susumu; Kirimura, Kotaro; Kino, Kuniki; Usami, Shoji.

    In: Journal of Bioscience and Bioengineering, Vol. 90, No. 6, 2000, p. 625-630.

    Research output: Contribution to journalArticle

    Sato, Toshiyuki ; Nakagawa, Hiroyuki ; Kurosu, Jun ; Yoshida, Keishiro ; Tsugane, Takanori ; Shimura, Susumu ; Kirimura, Kotaro ; Kino, Kuniki ; Usami, Shoji. / α-Anomer-selective glucosylation of (+)-catechin by the crude enzyme, showing glucosyl transfer activity, of Xanthomonas campestris WU-9701. In: Journal of Bioscience and Bioengineering. 2000 ; Vol. 90, No. 6. pp. 625-630.
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    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.",
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    T1 - α-Anomer-selective glucosylation of (+)-catechin by the crude enzyme, showing glucosyl transfer activity, of Xanthomonas campestris WU-9701

    AU - Sato, Toshiyuki

    AU - Nakagawa, Hiroyuki

    AU - Kurosu, Jun

    AU - Yoshida, Keishiro

    AU - Tsugane, Takanori

    AU - Shimura, Susumu

    AU - Kirimura, Kotaro

    AU - Kino, Kuniki

    AU - Usami, Shoji

    PY - 2000

    Y1 - 2000

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    AB - 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.

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    KW - Transglucosylation

    KW - Xanthomonas campestris

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