α-anomer-selective glucosylation of menthol with high yield through a crystal accumulation reaction using lyophilized cells of Xanthomonas campestris WU-9701

Hiroyuki Nakagawa, Yukio Dobashi, Toshiyuki Sato, Keishiro Yoshida, Takanori Tsugane, Susumu Shimura, Kotaro Kirimura, Kuniki Kino, Shoji Usami

    研究成果: Article

    22 引用 (Scopus)

    抄録

    l-Menthyl α-D-glucopyranoside (α-MenG) is a desirable derivative of l- menthol with useful properties for the production of new flavors and novel food additives. Bacteria were screened for α-anomer-selective glucosylation activity toward l-menthol, resulting in the isolation of two strains, Xanthomonas campestris WU-9701 and Stenotrophomonas maltophilia WU-9702, from independent soil samples. Since the safety of X. campestris for use in the food industry is well established, WU-9701 was selected as the more suitable strain for further study. When 50 mg X. campestris WU-9701 lyophilized cells as a biocatalyst were incubated with 1.0 M maltose and 100 mg l-menthol in 10 ml of 10 mM H3BO3 - NaOH - KCl buffer (pH 8.0) at 40°C, α-MenG was accumulated, mainly in a crystalline form, through the anomer-selective synthesis reaction without any by-product formation. Under the optimal conditions, 202 mg α-MenG was obtained over 48 h with a highest conversion yield of 99.1% based on the supplied l-menthol. Crude α-MenG formed through this 'crystal accumulation reaction' was easily collected from the reaction mixture by separation on filter paper. Plank-like crystals of purified α- MenG were subsequently obtained by recrystallization in ethyl acetate solution.

    元の言語English
    ページ(範囲)138-144
    ページ数7
    ジャーナルJournal of Bioscience and Bioengineering
    89
    発行部数2
    DOI
    出版物ステータスPublished - 2000

    Fingerprint

    Xanthomonas campestris
    Menthol
    Food additives
    Maltose
    Crystals
    Biocatalysts
    Flavors
    Byproducts
    Bacteria
    Stenotrophomonas maltophilia
    Crystalline materials
    Derivatives
    Soils
    Food Additives
    Food Industry
    Industry
    Buffers
    Soil
    Safety
    Enzymes

    ASJC Scopus subject areas

    • Biotechnology
    • Bioengineering

    これを引用

    α-anomer-selective glucosylation of menthol with high yield through a crystal accumulation reaction using lyophilized cells of Xanthomonas campestris WU-9701. / Nakagawa, Hiroyuki; Dobashi, Yukio; Sato, Toshiyuki; Yoshida, Keishiro; Tsugane, Takanori; Shimura, Susumu; Kirimura, Kotaro; Kino, Kuniki; Usami, Shoji.

    :: Journal of Bioscience and Bioengineering, 巻 89, 番号 2, 2000, p. 138-144.

    研究成果: Article

    Nakagawa, Hiroyuki ; Dobashi, Yukio ; Sato, Toshiyuki ; Yoshida, Keishiro ; Tsugane, Takanori ; Shimura, Susumu ; Kirimura, Kotaro ; Kino, Kuniki ; Usami, Shoji. / α-anomer-selective glucosylation of menthol with high yield through a crystal accumulation reaction using lyophilized cells of Xanthomonas campestris WU-9701. :: Journal of Bioscience and Bioengineering. 2000 ; 巻 89, 番号 2. pp. 138-144.
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    abstract = "l-Menthyl α-D-glucopyranoside (α-MenG) is a desirable derivative of l- menthol with useful properties for the production of new flavors and novel food additives. Bacteria were screened for α-anomer-selective glucosylation activity toward l-menthol, resulting in the isolation of two strains, Xanthomonas campestris WU-9701 and Stenotrophomonas maltophilia WU-9702, from independent soil samples. Since the safety of X. campestris for use in the food industry is well established, WU-9701 was selected as the more suitable strain for further study. When 50 mg X. campestris WU-9701 lyophilized cells as a biocatalyst were incubated with 1.0 M maltose and 100 mg l-menthol in 10 ml of 10 mM H3BO3 - NaOH - KCl buffer (pH 8.0) at 40°C, α-MenG was accumulated, mainly in a crystalline form, through the anomer-selective synthesis reaction without any by-product formation. Under the optimal conditions, 202 mg α-MenG was obtained over 48 h with a highest conversion yield of 99.1{\%} based on the supplied l-menthol. Crude α-MenG formed through this 'crystal accumulation reaction' was easily collected from the reaction mixture by separation on filter paper. Plank-like crystals of purified α- MenG were subsequently obtained by recrystallization in ethyl acetate solution.",
    keywords = "Anomer-selective reaction, Glucoside, Menthol, Stenotrophomonas maltophilia, Transglucosylation, Xanthomonas campestris",
    author = "Hiroyuki Nakagawa and Yukio Dobashi and Toshiyuki Sato and Keishiro Yoshida and Takanori Tsugane and Susumu Shimura and Kotaro Kirimura and Kuniki Kino and Shoji Usami",
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    T1 - α-anomer-selective glucosylation of menthol with high yield through a crystal accumulation reaction using lyophilized cells of Xanthomonas campestris WU-9701

    AU - Nakagawa, Hiroyuki

    AU - Dobashi, Yukio

    AU - Sato, Toshiyuki

    AU - Yoshida, Keishiro

    AU - Tsugane, Takanori

    AU - Shimura, Susumu

    AU - Kirimura, Kotaro

    AU - Kino, Kuniki

    AU - Usami, Shoji

    PY - 2000

    Y1 - 2000

    N2 - l-Menthyl α-D-glucopyranoside (α-MenG) is a desirable derivative of l- menthol with useful properties for the production of new flavors and novel food additives. Bacteria were screened for α-anomer-selective glucosylation activity toward l-menthol, resulting in the isolation of two strains, Xanthomonas campestris WU-9701 and Stenotrophomonas maltophilia WU-9702, from independent soil samples. Since the safety of X. campestris for use in the food industry is well established, WU-9701 was selected as the more suitable strain for further study. When 50 mg X. campestris WU-9701 lyophilized cells as a biocatalyst were incubated with 1.0 M maltose and 100 mg l-menthol in 10 ml of 10 mM H3BO3 - NaOH - KCl buffer (pH 8.0) at 40°C, α-MenG was accumulated, mainly in a crystalline form, through the anomer-selective synthesis reaction without any by-product formation. Under the optimal conditions, 202 mg α-MenG was obtained over 48 h with a highest conversion yield of 99.1% based on the supplied l-menthol. Crude α-MenG formed through this 'crystal accumulation reaction' was easily collected from the reaction mixture by separation on filter paper. Plank-like crystals of purified α- MenG were subsequently obtained by recrystallization in ethyl acetate solution.

    AB - l-Menthyl α-D-glucopyranoside (α-MenG) is a desirable derivative of l- menthol with useful properties for the production of new flavors and novel food additives. Bacteria were screened for α-anomer-selective glucosylation activity toward l-menthol, resulting in the isolation of two strains, Xanthomonas campestris WU-9701 and Stenotrophomonas maltophilia WU-9702, from independent soil samples. Since the safety of X. campestris for use in the food industry is well established, WU-9701 was selected as the more suitable strain for further study. When 50 mg X. campestris WU-9701 lyophilized cells as a biocatalyst were incubated with 1.0 M maltose and 100 mg l-menthol in 10 ml of 10 mM H3BO3 - NaOH - KCl buffer (pH 8.0) at 40°C, α-MenG was accumulated, mainly in a crystalline form, through the anomer-selective synthesis reaction without any by-product formation. Under the optimal conditions, 202 mg α-MenG was obtained over 48 h with a highest conversion yield of 99.1% based on the supplied l-menthol. Crude α-MenG formed through this 'crystal accumulation reaction' was easily collected from the reaction mixture by separation on filter paper. Plank-like crystals of purified α- MenG were subsequently obtained by recrystallization in ethyl acetate solution.

    KW - Anomer-selective reaction

    KW - Glucoside

    KW - Menthol

    KW - Stenotrophomonas maltophilia

    KW - Transglucosylation

    KW - Xanthomonas campestris

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