Automated synthesis of fluorinated β-D-mannuronic acid oligosaccharides to explore alginate structureproperty relationships

Alginate is a marine polysaccharide which forms gels with useful properties in the presence of water and divalent cations. There is great potential to derive sustainable materials with tailored properties from modified alginates, however the current understanding of how specific modifications affect the
conformations adopted by carbohydrates and their physical properties is limited. This is complicated by the difficulty in isolating individual defined carbohydrate species from natural sources for analysis. Herein, the synthesis of a small library of β-D-mannuronic acid oligosaccharides containing a 3-
deoxy-3-fluoro modification for use in alginate structure-property studies is reported. This was achieved using automated glycan assembly, an automated solid-phase approach to oligosaccharide synthesis. Towards this aim, two novel deoxyfluorinated D-mannuronic acid building blocks were synthesised on multigram scales, and their reactivity was investigated alongside that of a previously reported native D-mannuronic acid building block during low-temperature NMR experiments and solution-phase glycosylations. The synthesis of deoxyfluorinated mannose-1-phosphates, useful tools for the study of enzymes involved in alginate biosynthesis, and the attempted synthesis of an Lguluronic acid compound for attachment to biodegradable polymer supports is also detailed.

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