Design and synthesis of carba-sugars of biological interest

Abstract

Carba-sugars, carbocyclic analogues of true sugars, belong to a family of pseudo-sugars, which is currently attracting great interest among researchers in glycochemistry and glycobiology. The structures of carba-sugars very much resemble those of hexo- and pentopyranoses, but its reactivity and stability in vivo differs enormously from those of reducing sugars, mainly because it lacks the aldehyde or keto group. In particular, both natural and synthetic carba-glycosylamines have been shown to possess interesting biological properties in vivo as chemically-stable mimics of true glycosylamines. Moreover, several biologically interesting carba-oligosaccharides bonded by way of N- or O-linkage were designed and prepared on the basis of its unhydrolyzable features in vivo. Therefore, studies on carba-sugars will become one of the major plans for development of biologically active carbohydrate mimics as well as useful research tools for glycobiology.