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, Sho Yamasaki, Spencer J. Williams

    Research output: Contribution to journalArticle

    21 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

    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

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