Chemical characterization of milk oligosaccharides of the tiger quoll (Dasyurus maculatus), a marsupial

T Urashima, Tomoko Yamamoto, K Hirayama, K Fukuda, T Nakamura, T Saito, Keith Newgrain, J Merchant, Brian Green, M Messer

    Research output: Contribution to journalArticle

    3 Citations (Scopus)

    Abstract

    Milk oligosaccharides were separated from the carbohydrate fraction of milk of the tiger quoll a species of marsupial that is closely related to the eastern quoll, Dasyurus viverrinus. They were characterized by 1H – nuclear magnetic resonance spectroscopy and matrix – assisted laser desorption/ionization time-of-flight mass spectrometry. The following oligosaccharides were identified; Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–3)Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Neu5Ac(a2–3) Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc with an a(2–3)Neu5Ac linked to ß(1–4)Gal residue of either branch of Gal(ß1–4)GlcNAc(ß1–6) units, and Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc with a ß(1–3) linked Gal and an a(2–3) linked Neu5Ac. In addition, larger oligosaccharides were characterized as follows; Gal(ß1–3){Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)GlcNAc(ß1–6)}Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc and Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3){Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)GlcNAc(ß1–6)}Gal(ß1–4)Glc and their a(2–3) linked Neu5Ac derivatives.
    Original languageEnglish
    Pages (from-to)797-807
    Number of pages11
    JournalGlycoconjugate Journal
    Volume33
    Issue number5
    DOIs
    Publication statusPublished - 2016

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    Tigers
    Marsupialia
    Oligosaccharides
    Milk
    Nuclear magnetic resonance spectroscopy
    Ionization
    Mass spectrometry
    Desorption
    Mass Spectrometry
    Lasers
    Magnetic Resonance Spectroscopy
    Carbohydrates
    Derivatives

    Cite this

    Urashima, T., Yamamoto, T., Hirayama, K., Fukuda, K., Nakamura, T., Saito, T., ... Messer, M. (2016). Chemical characterization of milk oligosaccharides of the tiger quoll (Dasyurus maculatus), a marsupial. Glycoconjugate Journal, 33(5), 797-807. https://doi.org/10.1007/s10719-016-9675-1
    Urashima, T ; Yamamoto, Tomoko ; Hirayama, K ; Fukuda, K ; Nakamura, T ; Saito, T ; Newgrain, Keith ; Merchant, J ; Green, Brian ; Messer, M. / Chemical characterization of milk oligosaccharides of the tiger quoll (Dasyurus maculatus), a marsupial. In: Glycoconjugate Journal. 2016 ; Vol. 33, No. 5. pp. 797-807.
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    abstract = "Milk oligosaccharides were separated from the carbohydrate fraction of milk of the tiger quoll a species of marsupial that is closely related to the eastern quoll, Dasyurus viverrinus. They were characterized by 1H – nuclear magnetic resonance spectroscopy and matrix – assisted laser desorption/ionization time-of-flight mass spectrometry. The following oligosaccharides were identified; Gal({\ss}1–3)Gal({\ss}1–4)Glc, Gal({\ss}1–3)Gal({\ss}1–3)Gal({\ss}1–4)Glc, Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)Glc, Gal({\ss}1–3)Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)Glc, Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–3)Gal({\ss}1–4)Glc, Gal({\ss}1–3)[Gal({\ss}1–3)Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)Glc, Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)Glc, Neu5Ac(a2–3) Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)Glc, Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)Glc with an a(2–3)Neu5Ac linked to {\ss}(1–4)Gal residue of either branch of Gal({\ss}1–4)GlcNAc({\ss}1–6) units, and Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)Glc with a {\ss}(1–3) linked Gal and an a(2–3) linked Neu5Ac. In addition, larger oligosaccharides were characterized as follows; Gal({\ss}1–3){Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)GlcNAc({\ss}1–6)}Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)Glc and Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–3){Gal({\ss}1–3)[Gal({\ss}1–4)GlcNAc({\ss}1–6)]Gal({\ss}1–4)GlcNAc({\ss}1–6)}Gal({\ss}1–4)Glc and their a(2–3) linked Neu5Ac derivatives.",
    keywords = "Marsupials, Milk oligosaccharides, Tiger quoll",
    author = "T Urashima and Tomoko Yamamoto and K Hirayama and K Fukuda and T Nakamura and T Saito and Keith Newgrain and J Merchant and Brian Green and M Messer",
    year = "2016",
    doi = "10.1007/s10719-016-9675-1",
    language = "English",
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    pages = "797--807",
    journal = "Glycoconjugate Journal",
    issn = "0282-0080",
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    Urashima, T, Yamamoto, T, Hirayama, K, Fukuda, K, Nakamura, T, Saito, T, Newgrain, K, Merchant, J, Green, B & Messer, M 2016, 'Chemical characterization of milk oligosaccharides of the tiger quoll (Dasyurus maculatus), a marsupial', Glycoconjugate Journal, vol. 33, no. 5, pp. 797-807. https://doi.org/10.1007/s10719-016-9675-1

    Chemical characterization of milk oligosaccharides of the tiger quoll (Dasyurus maculatus), a marsupial. / Urashima, T; Yamamoto, Tomoko; Hirayama, K; Fukuda, K; Nakamura, T; Saito, T; Newgrain, Keith; Merchant, J; Green, Brian; Messer, M.

    In: Glycoconjugate Journal, Vol. 33, No. 5, 2016, p. 797-807.

    Research output: Contribution to journalArticle

    TY - JOUR

    T1 - Chemical characterization of milk oligosaccharides of the tiger quoll (Dasyurus maculatus), a marsupial

    AU - Urashima, T

    AU - Yamamoto, Tomoko

    AU - Hirayama, K

    AU - Fukuda, K

    AU - Nakamura, T

    AU - Saito, T

    AU - Newgrain, Keith

    AU - Merchant, J

    AU - Green, Brian

    AU - Messer, M

    PY - 2016

    Y1 - 2016

    N2 - Milk oligosaccharides were separated from the carbohydrate fraction of milk of the tiger quoll a species of marsupial that is closely related to the eastern quoll, Dasyurus viverrinus. They were characterized by 1H – nuclear magnetic resonance spectroscopy and matrix – assisted laser desorption/ionization time-of-flight mass spectrometry. The following oligosaccharides were identified; Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–3)Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Neu5Ac(a2–3) Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc with an a(2–3)Neu5Ac linked to ß(1–4)Gal residue of either branch of Gal(ß1–4)GlcNAc(ß1–6) units, and Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc with a ß(1–3) linked Gal and an a(2–3) linked Neu5Ac. In addition, larger oligosaccharides were characterized as follows; Gal(ß1–3){Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)GlcNAc(ß1–6)}Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc and Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3){Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)GlcNAc(ß1–6)}Gal(ß1–4)Glc and their a(2–3) linked Neu5Ac derivatives.

    AB - Milk oligosaccharides were separated from the carbohydrate fraction of milk of the tiger quoll a species of marsupial that is closely related to the eastern quoll, Dasyurus viverrinus. They were characterized by 1H – nuclear magnetic resonance spectroscopy and matrix – assisted laser desorption/ionization time-of-flight mass spectrometry. The following oligosaccharides were identified; Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–3)Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Neu5Ac(a2–3) Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc, Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc with an a(2–3)Neu5Ac linked to ß(1–4)Gal residue of either branch of Gal(ß1–4)GlcNAc(ß1–6) units, and Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc with a ß(1–3) linked Gal and an a(2–3) linked Neu5Ac. In addition, larger oligosaccharides were characterized as follows; Gal(ß1–3){Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)GlcNAc(ß1–6)}Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)Glc and Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–3){Gal(ß1–3)[Gal(ß1–4)GlcNAc(ß1–6)]Gal(ß1–4)GlcNAc(ß1–6)}Gal(ß1–4)Glc and their a(2–3) linked Neu5Ac derivatives.

    KW - Marsupials

    KW - Milk oligosaccharides

    KW - Tiger quoll

    U2 - 10.1007/s10719-016-9675-1

    DO - 10.1007/s10719-016-9675-1

    M3 - Article

    VL - 33

    SP - 797

    EP - 807

    JO - Glycoconjugate Journal

    JF - Glycoconjugate Journal

    SN - 0282-0080

    IS - 5

    ER -