Synthesis and Structural Analysis of Novel Bis(triazole) UDP Analogs as Potential Glycosyl Transferase Inhibitors

Abstract

The following details the synthesis of a novel bis(1,2,3-triazole), which is a potential glycosyltransferase inhibitor. A glycosyltransferase is an enzyme that is involved in the synthesis of polysaccharides, for example the capsule that protects Staphylococcus aureus. Bis(1,2,3-triazoles) may mimic the UDP conjugates of aminosugars (D-ManNAcA, D-FucNAc, and L-FucNAc) found in the capsular polysaccharide of S. aureus, and may prevent the formation of the capsular polysaccharide leaving the bacteria open to attack by phagocytosis or antibiotics. Bis(1,2,3-triazole) groups will be used to replace the phosphate linkages in the UDP-parent aminosugars. Bis(1,2,3-triazoles) may mimic the diphosphate linkage in binding to a transferase due to the N-3 lone pairs on the heterocycles.