Towards the synthesis of N-acetyl-2-amino-2-deoxy-D-mannopyranose uronic acid (D-ManNAcA) and derivatives

Abstract

The following details attempts at a stereoselective synthesis of deoxygenated D-mannose uronic acid derivatives from D-glucurono-6,3-lactone. These derivatives will be tested as potential inhibitors of enzymes used by Staphylococcus aureus to form its polysaccharide microcapsule, which functions as a protective barrier against destruction by the host. Two serotypes (types 5 and 8) compromise the majority of S. aureus bacteria and also the most virulent strains of this bacterium. The goal of this research project is to synthesize glycomimetics of D-ManNAcA that may act as potential inhibitors of the enzymes such as UDP-GlcNAc 2-epimerase. Since infections caused by S. aureus are an increasing threat in hospitals and the general community, it is of considerable interest within the biological community to find new treatments to combat these drug-resistant bacteria.