The steps needed to adapt a stable iodonium promoter for use in automated fluorous-assisted solution-phase oligosaccharide synthesis are described. Direct adaptation of the originally reported batch procedure resulted in the formation of an orthoester or protecting group transfer to the glycosyl acceptor. Fortunately, the addition of inexpensive β-pinene as an acid scavenger avoided both of these side reactions. The utility of this newly developed protocol was applied to the automated solution-phase synthesis of a β-glucan fragment.
The importance of oligosaccharides in myriad biological processes are becoming increasingly clear. However, these carbohydrate-mediated processes are often challenging to dissect due to the often poor affinity, stability and selectivity of the oligosaccharides involved. To circumvent these issues, non-natural carbohydrates—carbohydrate mimics—are being designed as innovative tools to modify biomolecules of interest or to understand biological pathways using fluorescence microscopy, X-ray or nuclear magnetic resonance spectroscopy (NMR). This review focuses on key examples of recently developed non-natural sugars to answer specific biological needs.
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