Precision Synthesis and Antiliver Fibrosis Activity of a Highly Branched Acidic 63-Mer Pectin Polysaccharide

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Natural polysaccharides possess various biological functions and have become increasingly important as drug candidates for biomedical development. However, the accessibility to multiple-branched and large-sized acidic polysaccharides with well-defined structures and the identification of related active glycan domains remain challenging. Here, we report the precision synthesis of a highly branched acidic pectin polysaccharide up to a 63-mer containing 10 different glycosidic linkages from Lycium barbarum . The synthetic strategy relies on highly stereoselective modular assembly of an orthogonally protected decasaccharide backbone, efficient synthesis of three side chain glycans by the integration of stereocontrolled one-pot chemoselective glycosylations and a hydrogen-bond-mediated aglycone delivery approach, and convergent assembly of the target polysaccharide in a branched site-specific glycosylation manner via flexible orthogonal protecting group manipulations. Structure–activity relationship studies of synthetic polysaccharide 63-mer and its short fragments (9-mer, 10-mer, 11-mer, and 33-mer) suggest that the decasaccharide as an active glycan domain exhibits better antiliver fibrosis activity.

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