Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
hemolytic-uremic syndrome (HUS) [ICD11:
3A21.2 ];
infection due to Escherichia coli [ICD11:
XN6P4 ]
NCBI PubMed ID: 23261778Publication DOI: 10.1016/j.carres.2012.11.009Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: I. Brockhausen <brockhau
queensu.ca>
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Medicine and Department of Biomedical and Molecular Sciences, Queen's University, Kingston, Canada
The assembly of the repeating units of O-antigens in Gram negative bacteria is catalyzed by specific glycosyltransferases. Previously we used GlcNAc/GalNAc?-diphosphate-phenoxyundecyl as natural acceptor substrate analogs in assays of the transfer of radioactive sugars by bacterial glycosyltransferases. In order to develop new, fluorescence based assays we have synthesized a fluorescent acceptor P(1)-[11-(anthracen-9-ylmethoxy)undecyl]-P(2)-(2-acetamido-2-deoxy-α-d-galactopyranosyl) diphosphate and have shown that the compound was an excellent acceptor for glucosyltransferase WbdN from Escherichia coli (E. coli) O157 and for galactosyltransferase WbwC from E. coli O5. This is the first report of the Gal-transferase activity of the wbwC gene product of E.coli O5. The presence of the fluorescent label in the acceptor molecule allows the detection of glycosyltransferase reaction products with high sensitivity, eliminating the need for radioactive nucleotide sugars.
Escherichia coli O157, glycosyltransferases, chemical synthesis, WbdN, fluorescent assay, E. coli O157, E. coli O5
Structure type: suggested polymer biological repeating unit
Location inside paper: p.17
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_136045,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_152214,IEDB_174333,IEDB_885822,IEDB_983931,SB_192,SB_86
Methods: 13C NMR, 1H NMR, glycosyltransferase assays, 31P NMR, MALDI-MS, chemical methods, biochemical methods, HPLC, TCL
Synthetic data: chemical and enzymatic
Related record ID(s): 1619, 7417, 8630, 8701, 8702, 8988, 20690, 28672, 28673, 28674, 28675, 30269, 30358, 105778, 108677
NCBI Taxonomy refs (TaxIDs): 1045010Reference(s) to other database(s): GTC:G60704LX, GlycomeDB:
27267
Show glycosyltransferases
There is only one chemically distinct structure:
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