Acyl group migration and cleavage in selectively protected β-d-galactopyranosides as studied by NMR spectroscopy and kinetic calculations

Mattias U. Roslund, Olli Aitio, Johan Wärnå, Hannu Maaheimo, Dmitry Yu. Murzin, Reko Leino

    Research output: Contribution to journalArticlepeer-review

    64 Citations (Scopus)

    Abstract

    The migration of acetyl, pivaloyl, and benzoyl protective groups and their relative stabilities at variable pH for a series of β-d-galactopyranoses were studied by NMR spectroscopy. The clockwise and counterclockwise migration rates for the different ester groups were accurately determined by use of a kinetic model. The results presented provide new insights into the acid and base stabilities of commonly used ester protecting groups and the phenomenon of acyl group migration and may prove useful in the planning of synthesis strategies.
    Original languageEnglish
    Pages (from-to)8769-8772
    Number of pages4
    JournalJournal of the American Chemical Society
    Volume130
    Issue number27
    DOIs
    Publication statusPublished - 2008
    MoE publication typeA1 Journal article-refereed

    Keywords

    • acyltransferases
    • acyl group
    • acyl group migration
    • esters
    • carbohydrate syntheses

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