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Synthesis of Streptococcus pneumoniae serotype 9V oligosaccharide antigens

MPS-Authors
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Parameswarappa,  Sharavathi Guddehalli
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Pereira,  Claney Lebev
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

/persons/resource/persons121849

Seeberger,  Peter H.
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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(Publisher version), 477KB

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Citation

Parameswarappa, S. G., Pereira, C. L., & Seeberger, P. H. (2020). Synthesis of Streptococcus pneumoniae serotype 9V oligosaccharide antigens. Beilstein Journal of Organic Chemistry, 16, 1693-1699. doi:10.3762/bjoc.16.140.


Cite as: http://hdl.handle.net/21.11116/0000-0006-CE61-5
Abstract
Streptococcus pneumoniae (SP) bacteria cause serious invasive diseases. SP bacteria are covered by a capsular polysaccharide (CPS) that is a virulence factor and the basis for SP polysaccharide and glycoconjugate vaccines. The serotype 9V is part of the currently marketed conjugate vaccine and contains an acetate modification. To better understand the importance of glycan modifications in general and acetylation in particular, defined oligosaccharide antigens are needed for serological and immunological studies. Here, we demonstrate a convergent [2 + 3] synthetic strategy to prepare the pentasaccharide repeating unit of 9V with and without an acetate group at the C-6 position of mannosamine.