Expeditious Synthesis of Bacterial Glycoconjugates

Session: 
S1.2 Bacterial glycan synthesis
Code: 
KL1.2
Location (hall): 
Mannose
Start/end time: 
Monday, July 1, 2019 - 11:15 to 11:45
Speaker reference: 
Suvarn
Kulkarni

Suvarn S. Kulkarni1

1Indian 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

References: 
  1. Emmadi, M.; Kulkarni, S. S. Nat. Prod. Rep. 2014, 31, 870-879.
  2. Behera, A.; Kulkarni, S. S. Molecules 2018, 23, 1997/1-1997/35.
  3. Emmadi, M.; Kulkarni, S. S. Nature Protocols 2013, 8, 1870-1889.
  4. Sanapala, S. R.; Kulkarni S. S. J. Am. Chem. Soc. 2016, 138, 4938−4947.
  5. Sanapala, S. R.; Kulkarni S. S. Org. Lett. 2016, 18, 3790–3793.
  6. Podilapu, A. R.; Kulkarni, S. S. Org. Lett. 2014, 16, 4336-4339.
  7. Sanapala, S. R.; Kulkarni, S. S., Chem. Eur. J. 2014, 20, 3578-3583.
  8. 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.
  9. Podilapu, A. R.; Kulkarni, S. S. Org. Lett. 2017, 19, 5466-5469.
  10. Behera, A.; Rai, D.; Kushwaha, D.; Kulkarni, S. S. Org. Lett. 2018, 20, 5956-5959.
  11. Kulkarni, S. S.*; Wang, C. C.;* Sabbavarapu, N. M.; Podilapu, A. R.; Liao, P. H.; Hung, S.-C.* Chem. Rev. 2018, 118, 8025–8104.

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