Synthesis of Rare Sugar Isomers through Site-Selective Epimerization

Alison Wendlandt reports on the synthesis of sugar isomers through site-selective epimerization.

Rare sugars (e.g. d-allose, d-gulose, d-talose, l-glucose) feature prominently in glycosylated natural products and find important applications in the pharmaceutical, cosmetic, and food industries. Current strategies for the synthesis of rare sugars from biomass carbohydrates (e.g. d-glucose, d-galactose, d-xylose, l-arabinose, sucrose) remain very limited, and often involve chemical or enzymatic isomerizations resulting in intractable thermodynamic product mixtures. Recent ground-breaking work from the group of Professor Alison Wendlandt from the Massachusetts Institute of Technology (Cambridge, USA) developed and validated a dual catalyst system capable of promoting a highly site-selective epimerization of secondary alcohols in a kinetically controlled manner, and ultimately transforms naturally abundant sugars into their rare counterparts.

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