Development of an analysis method for 4-Deoxy-L-erythro-5-hexoseulose uronic acid by LC/ESI/MS with selected ion monitoring

Toshiyuki Shibata, Reona Fujii, Hideo Miyake, Reiji Tanaka, Tetsushi Mori, Mami Takahashi, Toshiyuki Takagi, Hiroyuki Yoshikawa, Kouichi Kuroda, Mitsuyoshi Ueda

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    Abstract

    This study describes a simple and rapid analytical quantitative method for measuring 4-deoxy-L-erythro-5-hexoseulose uronic acid (DEH) using liquid chromatography-electrospray ionization-mass spectrometry (LC/ESI/MS). For a chromatographic condition, Shodex IC NI-424 column (4.6 mm i.d. x 100 mm, 5 μm) for anion analysis and an isocratic elution of 40 mM ammonium formate buffer including 0.1% formic acid (pH 3.75) at a flow rate of 0.5 mL/min was used. The column temperature was set to 40°C. In the analysis of DEH produced by exo-type alginate lyase (AlyFRB) from Falsirhodobacter sp. alg1, a peak was detected with a retention time of 3.207 min. The prepared calibration curves for DEH analysis using the selected ion monitoring (SIM) mode of a mass spectrometer revealed a good linear relationship (correlation factor: 0.9998) within the test range (0.1-100 μg/mL). The limits of detection (S/N = 3) and quantification (S/N = 10) for DEH in SIM analysis were 0.008 and 0.027 μg/mL, respectively. Using the developed condition of LC/ESI/MS analysis, separation and detection of alginate unsaturated oligosaccharides were also tested. In an analysis time of about 13 min, this method was able to separate and detect an alginate unsaturated disaccharide, a trisaccharide, and a tetrasaccaride produced by poly(β-D-mannuronate) lyase, respectively. The analysis method established in this study will contribute to the quantitative and qualitative analysis of DEH, and the activity measurement of exo-type alginate lyase.

    Original languageEnglish
    Pages (from-to)941-944
    Number of pages4
    JournalNatural Product Communications
    Volume12
    Issue number6
    Publication statusPublished - 2017

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    Keywords

    • 4-Deoxy-L-erythro-5-hexoseulose uronic acid
    • Alginate
    • Exo-type alginate lyase
    • Falsirhodobacter sp. alg1
    • Liquid chromatography-electrospray ionization-mass spectrometry

    ASJC Scopus subject areas

    • Medicine(all)
    • Pharmacology
    • Plant Science
    • Drug Discovery
    • Complementary and alternative medicine

    Cite this

    Shibata, T., Fujii, R., Miyake, H., Tanaka, R., Mori, T., Takahashi, M., Takagi, T., Yoshikawa, H., Kuroda, K., & Ueda, M. (2017). Development of an analysis method for 4-Deoxy-L-erythro-5-hexoseulose uronic acid by LC/ESI/MS with selected ion monitoring. Natural Product Communications, 12(6), 941-944.