Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Improved Synthesis of the Tetrasaccharide Repeat Unit of the O-Antigen Polysaccharide from Escherichia coli O77

  • Lee, Bo-Young (Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University) ;
  • Baek, Ju-Yuel (Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University) ;
  • Jeon, Heung-Bae (Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University) ;
  • Kim, Kwan-Soo (Center for Bioactive Molecular Hybrids and Department of Chemistry, Yonsei University)
  • Published : 2007.02.20
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Abstract

The efficient synthesis of a tetrasaccharide, the suitably protected form of the repeat unit, →2)-α-D-Manp-(1→2)-β-D-Manp-(1→3)-α-D-GlcpNAc-(1→6)-α-D-Manp-(1→, of the O-antigen polysaccharide of the lipopolysaccharide from E. coli O77 has been accomplished. Glycosylation reactions for the coupling of four monosaccharide building blocks of the tetrasaccharide were carried out employing the CB glycoside method, the mannosyl 4-pentenoate/PhSeOTf method, and the glycosyl trichloroacetimidate method with complete stereoselectivities in excellent yields.

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References

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