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, Kotaro Kirimura, Kuniki Kino, Shoji Usami

    Research output: Contribution to journalArticle

    65 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

    Fingerprint

    Arbutin
    Xanthomonas campestris
    Maltose
    Nuclear magnetic resonance
    Biocatalysts
    Cosmetics
    Glucosides
    hydroquinone
    Buffers
    Enzymes

    Keywords

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

    ASJC Scopus subject areas

    • Biotechnology
    • Bioengineering

    Cite this

    Enzymatic synthesis of α-arbutin by α-anomer-selective glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701. / Kurosu, Jun; Sato, Toshiyuki; Yoshida, Keishiro; Tsugane, Takanori; Shimura, Susumu; Kirimura, Kotaro; Kino, Kuniki; Usami, Shoji.

    In: Journal of Bioscience and Bioengineering, Vol. 93, No. 3, 2002, p. 328-330.

    Research output: Contribution to journalArticle

    Kurosu, Jun ; Sato, Toshiyuki ; Yoshida, Keishiro ; Tsugane, Takanori ; Shimura, Susumu ; Kirimura, Kotaro ; Kino, Kuniki ; Usami, Shoji. / Enzymatic synthesis of α-arbutin by α-anomer-selective glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701. In: Journal of Bioscience and Bioengineering. 2002 ; Vol. 93, No. 3. pp. 328-330.
    @article{e45b57bb7ada40e4840213c3a83d3774,
    title = "Enzymatic synthesis of α-arbutin by α-anomer-selective glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701",
    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{\%}.",
    keywords = "α-anomer-selective glucosylation, α-arbutin, Hydroquinone, Transglucosylation, Xanthomonas campestris",
    author = "Jun Kurosu and Toshiyuki Sato and Keishiro Yoshida and Takanori Tsugane and Susumu Shimura and Kotaro Kirimura and Kuniki Kino and Shoji Usami",
    year = "2002",
    doi = "10.1016/S1389-1723(02)80037-8",
    language = "English",
    volume = "93",
    pages = "328--330",
    journal = "Journal of Bioscience and Bioengineering",
    issn = "1389-1723",
    publisher = "Elsevier",
    number = "3",

    }

    TY - JOUR

    T1 - Enzymatic synthesis of α-arbutin by α-anomer-selective glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701

    AU - Kurosu, Jun

    AU - Sato, Toshiyuki

    AU - Yoshida, Keishiro

    AU - Tsugane, Takanori

    AU - Shimura, Susumu

    AU - Kirimura, Kotaro

    AU - Kino, Kuniki

    AU - Usami, Shoji

    PY - 2002

    Y1 - 2002

    N2 - 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%.

    AB - 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%.

    KW - α-anomer-selective glucosylation

    KW - α-arbutin

    KW - Hydroquinone

    KW - Transglucosylation

    KW - Xanthomonas campestris

    UR - http://www.scopus.com/inward/record.url?scp=0036098664&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=0036098664&partnerID=8YFLogxK

    U2 - 10.1016/S1389-1723(02)80037-8

    DO - 10.1016/S1389-1723(02)80037-8

    M3 - Article

    C2 - 16233209

    AN - SCOPUS:0036098664

    VL - 93

    SP - 328

    EP - 330

    JO - Journal of Bioscience and Bioengineering

    JF - Journal of Bioscience and Bioengineering

    SN - 1389-1723

    IS - 3

    ER -