Abstract

Expeditious Synthesis of Bacterial Glycoconjugates

Suvarn Kulkarni, Professor, Indian Institute of Technology Bombay

Bacterial glycoconjugates are comprised of rare D and L deoxy amino sugars, which are not present on the human cell surface. This peculiar structural difference allows discrimination between the pathogen and the host cell and offers avenues for target-specific drug discovery and carbohydrate-based vaccine development.  However, they cannot be isolated with sufficient purity in acceptable amounts, and therefore chemical synthesis is a crucial step toward the development of these products.1  We recently established short and convenient methodologies for the synthesis of orthogonally protected bacterial D and L-deoxy amino hexopyranoside  and glycosamine building blocks starting from cheaply available D-mannose and L-rhamnose.2-4  The one-pot protocols rely on highly regioselective nucleophilic displacements of triflates. These procedures have been applied to the synthesis of various bacterial glycoconjugates.