Glycosylation Chemistry of 3-Deoxy-D-manno-Oct-2-ulosonic Acid (Kdo) Donors

Abstract

3-Deoxy-D-manno-Oct-2-ulosonic acid (Kdo)-containing oligosaccharides are a conserved carbohydrate component in lipopolysaccharides ( LPSs) of the outer membrane of Gram-negative bacteria, and they are also present in capsular polysaccharides ( CPSs) of bacteria and plant cells. The association of the bacterial LPS with the pathophysiology of bacterial infection have long been recognized. Structure-pathophysiology studies of bacterial infection need to use pure and homogeneous LPS fragments. Such a requirement can be fulfilled by the synthesis of Kdo glycosides and related Kdo-oligosaccharide conjugates. This article provides an overview of the glycosylation chemistries of the synthesis of Kdo alpha-/beta-glycosides, oligosaccharides with Kdo units such as LPS core oligosaccharides, and lipid A derivatives.