Kalendář

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 glycoconjugates2–9 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.

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

Suvarn Kulkarni

Suvarn Kulkarni received his Ph.D. in Organic Chemistry from University of Pune in 2001. After his Ph. D., he pursued his post-doctoral research in the laboratory of Professor Shang-Cheng Hung at Academia Sinica, Taipei, on chemical synthesis of complex glycans via one-pot protection of sugars. In 2005, he moved to University of California Davis to work with Professsor Jacquelyn Gervay-Hague and was engaged in glycosyl iodide mediated one-pot synthesis of glycolipids.He returned to India in late 2008 and held a faculty position at IACS Kolkata prior to joining the Indian Institute of Technology Bombay in 2009. He subsequently rose to the rank of full professor in 2016. His current research interests include devising newer ways for efficient chemical synthesis of complex glycoconjugates implicated in various infectious diseases as well as cancer.Suvarn was a short term Visiting Professor (MOST) at Taiwan in 2014. Presently he is working as a vice president of RSC-WIS and is also a member of RSC Indian Sub-continent steering group committee. He is a Fellow of the Royal Society of Chemistry. He is a recipient of the CRSI Bronze medal for the year 2017 and Dr. H. C. Srivastava Young Scientist award 2016. He is a member of the editorial board of Carbohydrate Research. He was selected by the students for the best Teacher Award at IIT Bombay in 2017.

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

Zveme vás na 40. řádné zasedání Akademického senátu FCHI, které se bude konat 7.8. v 11:00 na sekretariátu ÚFCH - místnost A135.