Expeditious Synthesis of Bacterial Glycoconjugates

<none>

Programme Social programme Plenary speakers Keynote speakers 1st EuroCarb Young Researcher (ECYR) Workshop CarboMet Workshop Mini symposium: Glycobiology at the LUMC and beyond Favourites/Agenda

Social programme

Plenary speakers

Keynote speakers

1st EuroCarb Young Researcher (ECYR) Workshop

CarboMet Workshop

Mini symposium: Glycobiology at the LUMC and beyond

Favourites/Agenda

Photos

Venue & Travel Venue Accommodation City of Leiden Travel directions

Venue

Accommodation

City of Leiden

Travel directions

Committees

Home

Expeditious Synthesis of Bacterial Glycoconjugates

Suvarn S. Kulkarni 1

1 Indian Institute of Technology Bombay, Mumbai, India

Bacterial glycoconjugates are comprised of rare D and L deoxy amino sugars, which are not present on the human cell surface.[1] 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.[2] 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. 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.[3-5] The one-pot protocols rely on highly regioselective nucleophilic displacements of triflates. These procedures have been applied to the synthesis of various bacterial glycoconjugates.[3-10] (Figure 1) as well as metabolic oligosaccharide engineering for selective detection of bacteria.[8]

Figure 1. Representative examples of bacterial and archaeal glycans synthesized using the methodology

Emmadi, M.; Kulkarni, S. S. Nat. Prod. Rep. 2014, 31, 870-879.

Behera, A.; Kulkarni, S. S. Molecules 2018, 23, 1997/1-1997/35.

Emmadi, M.; Kulkarni, S. S. Nature Protocols 2013, 8, 1870-1889.

Sanapala, S. R.; Kulkarni S. S. J. Am. Chem. Soc. 2016, 138, 4938−4947.

Sanapala, S. R.; Kulkarni S. S. Org. Lett. 2016, 18, 3790–3793.

Podilapu, A. R.; Kulkarni, S. S. Org. Lett. 2014, 16, 4336-4339.

Sanapala, S. R.; Kulkarni, S. S., Chem. Eur. J. 2014, 20, 3578-3583.

Clark, E.; I.; Emmadi, M.; Krupp, K. L.; Podilapu, A. R.; Helble, J. D.; Kulkarni, S. S.; Dube, D. H. ACS Chem Biol 2016, 11, 3365-3373.

Podilapu, A. R.; Kulkarni, S. S. Org. Lett. 2017, 19, 5466-5469.

Behera, A.; Rai, D.; Kushwaha, D.; Kulkarni, S. S. Org. Lett. 2018, 20, 5956-5959.

Kulkarni, S. S.*; Wang, C. C.;* Sabbavarapu, N. M.; Podilapu, A. R.; Liao, P. H.; Hung, S.-C.* Chem. Rev. 2018, 118, 8025–8104.

Contact eurocarb@eurocarb2019.com for general questions about EUROCARB2019, or codee@eurocarb2019.com for scientific questions.

Leiden University / Leiden Institute of Chemistry lic.leidenuniv.nl

European Carbohydrate Organisation

Congress by Design www.congressbydesign.com