Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperPublication DOI: 10.1016/S0008-6215(00)90428-2Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Division of Plant Industry, CSIRO, Canberra, Australia, Division of Entomology, CSIRO, Canberra, Australia
Twelve bacterial polysaccharides of known structure containing a representative range of pyruvated monosaccharides, were methanolysed, trimethylsilylated, and analysed by g.l.c. and g.l.c.-m.s. Except for 3,4-O-(1-carboxyethylidene)-l-rhamnose, which was unusually labile, the pyruvic acid substituents were largely retained during methanolysis and the Me3Si derivatives of the resulting pyruvated methyl glycosides gave distinctive g.l.c. peaks with characteristic mass spectra. The pyranose rings of 4,6-O-(1-carboxyethylidene)-d-glucose, 4,6-O-(1-carboxyethylidene)-d-mannose, 4,6-O-(1-carboxyethylidene)-d-galactose, and 3,4-O-(1-carboxyethylidene)-d-galactose survived the methanolysis, but that of 2,3-O-(1-carboxyethylidene)-d-glucuronic acid was cleaved to give the methyl ester of 2,3-O-(1-carboxyethylidene)-aldehydo-d-glucuronic acid dimethyl acetal. In the case of 2,3-O-(1-carboxyethylidene)-d-galactose, cleavage of the pyranose ring was less complete; under the conditions used in these experiments two-thirds of the pyranose rings were intact while one-third were cleaved to give the methyl ester of 2,3-O-(1-carboxyethylidene)-aldehydo-d-galactose dimethyl acetal. A very small amount of 3,4-O-(1-carboxyethylidene)-l-rhamnose from one polysaccharide retained its pyruvic acid substituent after gentle methanolysis to give the methyl ester of 3,4-O-(1-carboxyethylidene)-aldehydo-l-rhamnose dimethyl acetal. Susceptibility to cleavage of the pyranose ring during methanolysis appears to be a property of pyruvated monosaccharides with trans-fused 1,3-dioxolane rings.
Structure type: oligomer
Location inside paper: D
Compound class: K-antigen
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136045,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_151771,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_423153,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88
Methods: GLC-MS, methanolysis, CC
Related record ID(s): 114550, 114551, 114552, 114554, 114555, 114556, 114557, 114558, 114559, 114560
NCBI Taxonomy refs (TaxIDs): 83333
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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