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Journal Article

Total synthesis of a Streptococcus pneumoniae serotype 12F CPS repeating unit hexasaccharide

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

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

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Fulltext (public)

2387721.pdf
(Publisher version), 649KB

Supplementary Material (public)

2387721_supp.pdf
(Supplementary material), 6MB

Citation

Seeberger, P. H., Pereira, C. L., & Govindan, S. (2017). Total synthesis of a Streptococcus pneumoniae serotype 12F CPS repeating unit hexasaccharide. Beilstein Journal of Organic Chemistry, 13, 164-173. doi:10.3762/bjoc.13.19.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002C-514D-6
Abstract
The Gram-positive bacterium Streptococcus pneumoniae causes severe disease globally. Vaccines that prevent S. pneumoniae infections induce antibodies against epitopes within the bacterial capsular polysaccharide (CPS). A better immunological understanding of the epitopes that protect from bacterial infection requires defined oligosaccharides obtained by total synthesis. The key to the synthesis of the S. pneumoniae serotype 12F CPS hexasaccharide repeating unit that is not contained in currently used glycoconjugate vaccines is the assembly of the trisaccharide β-D-GalpNAc-(1→4)-[α-D-Glcp-(1→3)]-β-D-ManpNAcA, in which the branching points are equipped with orthogonal protecting groups. A linear approach relying on the sequential assembly of monosaccharide building blocks proved superior to a convergent [3 + 3] strategy that was not successful due to steric constraints. The synthetic hexasaccharide is the starting point for further immunological investigations.