O-acetyl-galactoglucomannan (GGM) is the main hemicellulose in industrially important softwood species and can be isolated in large scale, for example, from the waste waters of mechanical pulping. GGM is a potential raw material for natural biochemicals. The physicochemical properties of polysaccharides can be improved by introducing functional groups to the molecule. Targeted modification is obtained by combining enzymatic oxidation and chemical modification. Metal mediated allylation of aldehydes produces homoallylic alcohols, typically in high yields. The reaction can be done in aqueous media, thus carbohydrates are modified without protection of the hydroxyls. Drying and isolation steps are avoided and GGM is derivatized as a one-pot reaction. The double or triple bonds introduced by the reaction can be further derivatized. Indium mediated allylation of enzymatically oxidized GGM, guar gum, and xyloglucan was investigated. Allyl bromide, propargyl bromide, cinnamyl chloride, and crotyl chloride were tested for incorporation of functional groups to the polysaccharides.

Targeted modification of galactose-containing polysaccharides

243rd National Meeting (2012)

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