Convergent synthesis of degradable dendrons based on L-malic acid

Ulrich Meyhoff, Ulla Riber, Ulrik Boas

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    New degradable polyester dendrons based on the cellular tricarboxylic acid cycle component L-malic acid were synthesized up to the third generation by convergent synthesis. The dendron wedges could be introduced in a stepwise, highly regioselective fashion. HMBC-NMR revealed that the C1-carbonyl on malic acid was exclusively esterified, before the reaction of the second dendron wedge at C4 took place. Degradation studies on a first generation dendron analyzed by HPLC showed that hydrolytic degradation of the dendron most profoundly takes place at pH 4 and pH 9 with the highest degradation rate at alkaline pH. NMR shows that the dendron degrades to malic acid and fumaric acid derivatives. Preliminary studies performed in the cell culture show low toxicity of the dendrons in concentrations of up to 50 μg mL-1.
    Original languageEnglish
    JournalNew Journal of Chemistry
    Volume39
    Issue number2
    Pages (from-to)1161-1171
    ISSN1144-0546
    DOIs
    Publication statusPublished - 2015

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