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Biological Chemistry

Amide-Linked Polysaccharide

Method substitutes amide linkers for ethers, making controlled production of derivatives of natural sugar biomolecules possible

by Elizabeth K. Wilson
October 8, 2012 | APPEARED IN VOLUME 90, ISSUE 41

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Credit: J. Am. Chem. Soc.
A computer simulation predicts the structure of a polysaccharide that substitutes an amide for ether linkages.
09041-scicon-polysaccharide.jpg
Credit: J. Am. Chem. Soc.
A computer simulation predicts the structure of a polysaccharide that substitutes an amide for ether linkages.

Scientists have developed a method for synthesizing polysaccharides with units linked by amide groups instead of ethers, giving researchers a new tool to generate well-defined mimics of these key biomacromolecules (J. Am. Chem. Soc., DOI: 10.1021/ja305900r). Boston University’s Mark W. Grinstaff and Eric L. Dane produced the polyamidosaccharides via an anionic ring-opening polymerization of a strained β-lactam prepared from d-glucal, a glucose derivative. Like other large biomolecules, such as nucleic acids and peptides, polysaccharides play innumerable roles in biology and technology. For example, the sulfated polysaccharide heparin is used as an anticoagulant, and protein-bound polysaccharides are used in cancer therapy. Yet their synthesis has proved challenging. The new polysaccharides show promise as natural polysaccharide mimics, Grinstaff says, noting that they bind the lectin concanavalin A at the same site that natural polysaccharides bind. Grinstaff hopes the method will allow polysaccharide research to blossom in the same manner as research on other biomolecules. “I would like to think that we have the same opportunity here with further development,” he says.

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