Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
enterohemorrhagic disease [ICD11:
1A03.3 , ICD11:
XN6P4 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
NCBI PubMed ID: 23447496Publication DOI: 10.1002/chem.201204394Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: peter.seeberger
mpikg.mpg.de
Institutions: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476 Potsdam (Germany) and Institute for Chemistry and Biochemistry, Freie Universitat Berlin, Arnimallee 22, 14195 Berlin (Germany), Fax: (+49) 331-567-9302
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.
carbohydrates, Escherichia coli, antigens, vaccines, glycosylation
Structure type: polymer chemical repeating unit
Location inside paper: p.3995, fig.1
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_983931,SB_192,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, chemical synthesis, chemical methods, MALDI-TOF MS
Synthetic data: chemical
Related record ID(s): 29436
NCBI Taxonomy refs (TaxIDs): 1055535Reference(s) to other database(s): GTC:G38677MM, GlycomeDB:
3515
Show glycosyltransferases
There is only one chemically distinct structure:
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