The glycero-D-mannoheptose core structure is exclusively found in bacteria, either with the 6-D configuration as in 1 or with a 6-L configuration as in ADP-heptose 3. Nucleotide-sugar 3 is the substrate of bacterial heptosyltransferases that play a key role in the biosynthesis of Lipopolysaccharide (LPS). From a medical this bacterial biosynthetic pathway is important because: 1) the inhibition of the heptose processing enzymes leads to a dramatic phenotypic change that blocks the virulence of some major pathogenic gram-negative bacteria 2) It has been recently shown that heptose metabolites such as 1-3 can activate the innate immune response through a TIFA-dependent pathway.[1] HBP 1 and ADP-heptose 2 have been identified as Pathogen-Associated Molecular Patterns (PAMPS) for important bacterial pathogens such as Helicobacter pylori. Based on the biological relevance of the bacterial heptosides, our laboratory has synthesized different types of heptose glycomimetics illustrated in Figure 1: multivalent species based on a glycofullerene core structure 4,[2] highly fluorinated D-heptoside 5 and heptosyltransferase inhibitor 6.[3] Novel heptose scaffolds are now available in our laboratory and their biological evaluations will be discussed. Similar molecular probes have been also used in our laboratory to study the host-pathogen interaction of SARS-CoV-2 and its receptors.[4]

Glycomimetics as probes of bacterial and viral infections

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.