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Total Synthesis of the Escherichia coli O111 O ‐Specific Polysaccharide Repeating Unit
Author(s) -
Calin Oliviana,
Eller Steffen,
Hahm Heung Sik,
Seeberger Peter H.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204394
Subject(s) - escherichia coli , polysaccharide , chemistry , unit (ring theory) , microbiology and biotechnology , biochemistry , biology , mathematics , mathematics education , gene
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.