Alginate, an anionic polysaccharide, is an important industrial biomaterial naturally harvested from seaweed. Many of its important physicochemical properties derive from the presence of charged carboxylate groups, presented as uronic acids, within the polysaccharide backbone. An ability to design and synthesise isosteres of these carboxylates would ultimately enable access to new alginate systems possessing different physicochemical properties. We present herein an approach to the chemical synthesis of alginate building blocks, modified at the carboxylate C6 position with bioisosteric tetrazole. The development of this synthesis enables utilisation of C6-tetrazole donors to deliver anomeric phosphate and 3-aminopropyl free sugars containing this motif. Access to these building blocks will further enable glycosylation methodologies to be explored that incorporate tetrazole as a bioisostere within uronic acid-containing carbohydrates.
Keywords: alginate; tetrazole; non-native monosaccharide; glycosyl 1-phosphate; uronate
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Dimitriou, E.; Miller, G. J. Beilstein Arch. 2021, 202125. doi:10.3762/bxiv.2021.25.v1
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