Most pathogens including bacteria, fungi, viruses and protozoa carry unique glycans on their surface. Currently, several vaccines against bacteria are marketed very successfully. Since many pathogens cannot be cultured and the isolation of pure oligosaccharides is extremely difficult, synthetic oligosaccharide antigens provide now a viable alternative. Based on the automated synthesis platform,(1) that has now been completely overhauled,(2) we are currently developing multiple vaccine candidates against bacterial infections, fungi, and protozoan parasites. In addition to their function as antigens, the synthetic oligosaccharides serve as tools to create monoclonal antibodies, and to establish glycan microarrays to map vaccine epitopes.(3) In this lecture N. meningitides, C. difficile and S. pneumoniae will be used as examples to illustrate the approach. (4,5)Traditionally, chemists have performed reactions in a batch-wise mode. In recent years continuous flow systems have become increasingly interesting to practitioners of synthetic chemistry. (6) Described is the use of a continuous flow system to produce the anti-malaria drug artemisinin as well as its derivatives that are used as the basis for artemisinin combination therapies (ACTs) in large quantities.(7,8)References:1. Plante, O.J.; Palmacci, E.R.; Seeberger, P.H.; Science 2001 , 291, 1523.2. Castagner, B.; Kr�ck, L.; Esposito, D.; Wang, C.-C.; Bindsch�dler, P.; Seeberger, P.H.; Chem. Sci. 2012 , 3, 1617.3. Ratner, D.M.; Adams, E.W.; Su, J.; O'Keefe, B.R.; Mrksich, M.; Seeberger, P.H.; ChemBioChem. 2004 , 5, 379. Kamena, F.; Tamborrini, M.; Liu, X.; Kwon, Y.-U.; Thompson, F.; Pluschke, G.; Seeberger; P.H.; Nature Chem. Bio., 2008 , 4, 238.4. Martin, C.E.; Weishaupt, M.W.; Seeberger, P.H.; Chem. Comm. 2011 , 47, 10260.5. Yang, Y.; Martin, C.E.; Seeberger, P.H.; Chem. Sci. 2012 , 3, 896; Yang, Y.; Oishi, S.; Martin, C.; Seeberger, P.H.; J. Am. Chem. Soc. 2013 , 135, 6262.6. Geyer, K.; Codee, J.D.C.; Seeberger, P.H.; Chem. Eur. J. 2006 , 12, 8434.7. Levesque, F.; Seeberger, P.H. Angew. Chem. Int. Ed. 2012 , 51, 1706.8. Kopetzki, D.; L�vesque, F.; Seeberger, P.H.; Chem Eur. J. 2013 , 19, 5450

Preventing and curing infectious diseases: Carbohydrate vaccines and continuous flow synthesis

247th National Meeting (2014)

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