Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 12, Pages 3995-4002Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201204394
Keywords
antigens; carbohydrates; Escherichia coli; glycosylation; vaccines
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Funding
- Max-Planck Society
- Marie Curie ITN FP7 project CARMUSYS [PITN-GA-2008-213592]
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The first total synthesis of the O-antigen pentasaccharide repeating unit from Gram-negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis-glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non-carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.
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