Recent developments in glycosyl urea synthesis

Abstract

The area of sugar urea derivatives has received considerable attention in recent years because of the unique structural properties and activities that these compounds display. The urea-linkage at the anomeric center is a robust alternative to the naturally occurring O- and N-glycosidic linkages of oligosaccharides and glycoconjugates, and the natural products that have been identified to contain these structures show remarkable biological activity. While methods for installing the β-urea-linkage at the anomeric center have been around for decades, the first synthesis of α-urea glycosides has been much more recent. In either case, the selective synthesis of glycosyl ureas can be quite challenging, and a mixture of α- and β-isomers will often result. This paper will provide a comprehensive review of the synthetic approaches to α- and β-urea glycosides and examine the structure and activity of the natural products and their analogues that have been identified to contain them.

Keywords: Carbohydrate; Neoglycoconjugate; Pseudooligosaccharide; Rearrangement; Stereoselectivity; Urea.