Targeted allylation and propargylation of galactose-containing polysaccharides in water

Ann-Sofie Leppänen, Chunlin Xu, Kirsti Parikka, Patrik Christoffer Eklund, Rainer Sjöholm, Harry Brumer, Maija Tenkanen, Stefan Willför

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    Abstract

    Galactose units of spruce galactoglucomannan (GGM), guar galactomannan (GM), and tamarind (galacto)xyloglucan (XG) were selectively allylated. Firstly aldehyde functionalities were formed at the C-6 position via enzymatic oxidation by galactose oxidase. The formed aldehydes were further derivatized by an indium mediated Barbier-Grignard type reaction, resulting in the formation of homoallylic alcohols. In addition to allylic halides, the same reaction procedure was also applicable for GGM, when using propargyl bromide as halide. All reaction steps were done in water, thus the polysaccharides were modified in a one-pot reaction. The formation of the allylated, or propargylated, product was identified by MALDI-TOF-MS. All polysaccharide products were isolated and further characterized by GC-MS or NMR spectroscopy. By this chemo-enzymatic process, we have demonstrated a novel method for derivatization of GGM and other galactose-containing polysaccharides. The derivatized polysaccharides are potential platforms for further functionalizations.
    Original languageUndefined/Unknown
    Pages (from-to)46–54
    JournalCarbohydrate Polymers
    Volume100
    DOIs
    Publication statusPublished - 2014
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Polysaccharides
    • Spruce galactoglucomannan
    • Guar galactoglucomannan
    • Tamarind xyloglucan
    • Allylation
    • Propargylation
    • Indium mediated
    • MALDI-TOF-MS

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