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

    Research output: Contribution to journalArticle

    22 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)138-144
    Number of pages7
    JournalJournal of Bioscience and Bioengineering
    Volume89
    Issue number2
    DOIs
    Publication statusPublished - 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

    Keywords

    • Anomer-selective reaction
    • Glucoside
    • Menthol
    • Stenotrophomonas maltophilia
    • Transglucosylation
    • Xanthomonas campestris

    ASJC Scopus subject areas

    • Biotechnology
    • Bioengineering

    Cite this

    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.

    In: Journal of Bioscience and Bioengineering, Vol. 89, No. 2, 2000, p. 138-144.

    Research output: Contribution to journalArticle

    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. In: Journal of Bioscience and Bioengineering. 2000 ; Vol. 89, No. 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.",
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    AU - Dobashi, Yukio

    AU - Sato, Toshiyuki

    AU - Yoshida, Keishiro

    AU - Tsugane, Takanori

    AU - Shimura, Susumu

    AU - Kirimura, Kotaro

    AU - Kino, Kuniki

    AU - Usami, Shoji

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    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.

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