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Issue 3, 2012
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Total synthesis of the core tetrasaccharide of Neisseria meningitidislipopolysaccharide, a potential vaccine candidate for meningococcal diseases

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Abstract

The first total synthesis of the core tetrasaccharide α-GlcNAc-(1 → 2)-α-Hep-(1 → 3)-α-Hep-(1 → 5)-α-Kdo of Neisseria meningitidis LPS is achieved in a convergent and stereocontrolled [2 + 2] approach, whereby heptose building blocks obtained by de novo synthesis were fine-tuned for the effective assembly of the 1 → 5 linked Hep-Kdo disaccharide. The synthetic strategy incorporates an α-linked spacer at the reducing end of the tetrasaccharide for use as a handle during subsequent conjugation to a carrier protein.

Graphical abstract: Total synthesis of the core tetrasaccharide of Neisseria meningitidislipopolysaccharide, a potential vaccine candidate for meningococcal diseases

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Publication details

The article was received on 14 Oct 2011, accepted on 18 Nov 2011 and first published on 08 Dec 2011


Article type: Edge Article
DOI: 10.1039/C1SC00804H
Citation: Chem. Sci., 2012,3, 896-899
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    Total synthesis of the core tetrasaccharide of Neisseria meningitidislipopolysaccharide, a potential vaccine candidate for meningococcal diseases

    Y. Yang, C. E. Martin and P. H. Seeberger, Chem. Sci., 2012, 3, 896
    DOI: 10.1039/C1SC00804H

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