Total synthesis of a cyclopropane-fatty acid α-glucosyl diglyceride from: Lactobacillus plantarum and identification of its ability to signal through Mincle

Sayali Shah, Masahiro Nagata, Shou Yamasaki, Spencer J. Williams

    Research output: Contribution to journalArticle

    17 Citations (Scopus)

    Abstract

    We report a concise synthesis of glycolipid GL1 from Lactobacillus plantarum commencing from methyl α-d-glucopyroside. A Jacobsen hydrolytic kinetic resolution is used to generate a diastereomerically-pure glycidyl glucoside that was elaborated to the diglyceride by stepwise brominolysis, acylation with oleoyl chloride, and bromide-substitution by the tetrabutylammonium salt of 9S,10R-dihydrosterculic acid. GL1 and analogues were shown to signal through the glycolipid pattern recognition receptor Mincle.

    Original languageEnglish
    Pages (from-to)10902-10905
    Number of pages4
    JournalChemical Communications
    Volume52
    Issue number72
    DOIs
    Publication statusPublished - Jan 1 2016

    Fingerprint

    Glycolipids
    Diglycerides
    Fatty acids
    Pattern Recognition Receptors
    Acylation
    Glucosides
    Bromides
    Pattern recognition
    Chlorides
    Substitution reactions
    Salts
    Kinetics
    Acids
    cyclopropane fatty acids
    tetrabutylammonium
    dihydrosterculic acid

    All Science Journal Classification (ASJC) codes

    • Catalysis
    • Electronic, Optical and Magnetic Materials
    • Ceramics and Composites
    • Chemistry(all)
    • Surfaces, Coatings and Films
    • Metals and Alloys
    • Materials Chemistry

    Cite this

    Total synthesis of a cyclopropane-fatty acid α-glucosyl diglyceride from : Lactobacillus plantarum and identification of its ability to signal through Mincle. / Shah, Sayali; Nagata, Masahiro; Yamasaki, Shou; Williams, Spencer J.

    In: Chemical Communications, Vol. 52, No. 72, 01.01.2016, p. 10902-10905.

    Research output: Contribution to journalArticle

    Shah, Sayali ; Nagata, Masahiro ; Yamasaki, Shou ; Williams, Spencer J. / Total synthesis of a cyclopropane-fatty acid α-glucosyl diglyceride from : Lactobacillus plantarum and identification of its ability to signal through Mincle. In: Chemical Communications. 2016 ; Vol. 52, No. 72. pp. 10902-10905.
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