Synthesis of Sugar Nucleotides by Application of Phosphoramidites

H. Gold, P. van Delft, N. Meeuwenoord, J.D.C. Codee, D.V. Filippov, G. Eggink, H.S. Overkleeft, G.A. van der Marel

    Research output: Contribution to journalArticleAcademicpeer-review

    37 Citations (Scopus)

    Abstract

    new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate¿phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.
    Original languageEnglish
    Pages (from-to)9458-9460
    JournalJournal of Organic Chemistry
    Volume73
    Issue number23
    DOIs
    Publication statusPublished - 2008

    Keywords

    • potential chain-terminators
    • udp-glcnac analogs
    • chemical-synthesis
    • nucleoside polyphosphates
    • efficient synthesis
    • gdp-fucose
    • derivatives
    • glycosyltransferases
    • biosynthesis
    • galactose

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