March 28, 1994 - March 28, 2027

  • Date:16TuesdayOctober 2018

    Expeditious Synthesis of Bacterial Glycoconjugates

    More information
    Time
    11:00 - 12:00
    Location
    Helen and Milton A. Kimmelman Building
    Dov Elad Room
    Lecturer
    Prof. Suvarn S. Kulkarni
    Indian Institute of Technology Bombay
    Organizer
    Department of Molecular Chemistry and Materials Science
    Contact
    AbstractShow full text abstract about Expeditious Synthesis of Bacterial Glycoconjugates Suvarn ...»
    Expeditious Synthesis of Bacterial Glycoconjugates
    Suvarn S. Kulkarni
    Department of Chemistry, IIT Bombay, Powai, Mumbai-400076
    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 glycoconjugates2-8 (Figure 1) as well as metabolic oligosaccharide engineering.7


    1) Emmadi, M.; Kulkarni, S. S. Nat. Prod. Rep. 2014, 31, 870-879. 2) Emmadi, M.; Kulkarni, S. S. Nature Protocols 2013, 8, 1870-1889. 3) Sanapala, S. R.; Kulkarni S. S. J. Am. Chem. Soc. 2016, 138, 4938−4947. 4) Sanapala, S. R.; Kulkarni S. S. Org. Lett. 2016, 18, 3790–3793. 5) Podilapu, A. R.; Kulkarni, S. S. Org. Lett. 2014, 16, 4336-4339. 6) Sanapala, S. R.; Kulkarni, S. S., Chem. Eur. J. 2014, 20, 3578-3583. 7) 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. 8) Podilapu, A. R.; Kulkarni, S. S. Org. Lett. 2017, 19, 5466-5469.
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