Abstract
We designed multiple Small Cluster Oligosaccharide Mimetics (SCOMs) - potential glycosidase inhibitors - to be metabolically stable and small enough to enter cells or bacteria. Therefore, minimal scaffolds (urea, amide, ammonia) or simply non-glycosidic linkages of carbohydrate structures were central to our synthetic strategy, including: (a) coupling of several natural carbohydrate precursors; (b) total syntheses of aminomethyl tetrahydropyrans and their chiral amides with quinic acid; (c) glycopyranosyl cyanide reduction to prepare crowded clusters on a urea scaffold; (d) total syntheses via cycloadditions leading to amide-linked C-glycosides; (e) reduction of nitromethyl C-glycosides; and (f) a synthesis of hydroxylated 1,2- cyclohexanedicarboxylic acids.
Highlights
After the early years of carbohydrate chemistry around 1900 and Emil Fischer’s structure proof of the carbohydrates, this area of chemistry received only little attention
Quinamide Small Cluster Oligosaccharide Mimetics (SCOMs) synthesized through nucleophilic opening of quinic lactone.[47,48,49]
We have developed a synthesis of acetylated glycosyl bromides and subsequently glycals from per-acetylated sugars under non-solvolytic conditions.[62,63,64]
Summary
After the early years of carbohydrate chemistry around 1900 and Emil Fischer’s structure proof of the carbohydrates, this area of chemistry received only little attention. Monosaccharide units combine to oligosaccharides in an almost infinite number of permutations, determined by the stereochemical identity of the linked monosaccharides (e.g. glucose, galactose, mannose), their glycosidic linkage position (e.g. 1→4, 1→6), their anomericity (α or β), and the overall degree of branching. This complexity, further increased by additional modifications such as sulfation or sialation, was suggested recently to serve the evolutionary purpose of “herd immunity”.15,16.
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