Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter jejuni [ICD11:
XN4Q5 
]
The structure was elucidated in this paperNCBI PubMed ID: 19282391Publication DOI: 10.1093/glycob/cwp039Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: ian.schoenhofen
nrc-cnrc-gc.ca
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Ontario, Canada K1A 0R6
The sialic acid-like sugar 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulosonic acid, or legionaminic acid, is found as a virulence-associated cell-surface glycoconjugate in the Gram-negative bacteria Legionella pneumophila and Campylobacter coli. L. pneumophila serogroup 1 strains, causative agents of Legionnaire's disease, contain an α2,4-linked homopolymer of legionaminic acid within their lipopolysaccharide O-chains, whereas the gastrointestinal pathogen C. coli modifies its flagellin with this monosaccharide via O-linkage. In this work, we have purified and biochemically characterized eleven candidate biosynthetic enzymes from C. jejuni, thereby fully reconstituting the biosynthesis of legionaminic acid and its CMP-activated form, starting from fructose-6-P. This pathway involves unique GDP-linked intermediates, likely providing a cellular mechanism for differentiating between this and similar UDP-linked pathways, such as UDP-2,4-diacetamido-bacillosamine biosynthesis involved in N-linked protein glycosylation. Importantly, these findings provide a facile method for efficient large-scale synthesis of legionaminic acid, and since legionaminic acid and sialic acid share the same D-glycero-D-galacto absolute configuration, this sugar may now be evaluated for its potential as a sialic acid mimic.
Campylobacter jejuni, sialic acid, legionaminic acid, flagellin glycosylation, neuraminic aid
Structure type: monomer
Location inside paper: p.717, fig.2,II
Trivial name: GlcN-6-P
Contained glycoepitopes: IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, SDS-PAGE, genetic methods, biochemical methods, capillary electrophoresis (CE), CE-MS
Biological activity: kenetic data,substrat specificity data
Enzymes that release or process the structure: PtmF,glutaminase/PtmA,isomerase (GlcN-6-P synthase,GlmS)
Synthetic data: enzymatic
Comments, role: GlcN-6-P was obtained in the presence or absence of L-glutamine.
Related record ID(s): 23836, 24208, 24209, 24210, 24211, 24212, 24213, 24214, 24215, 24216, 24288
NCBI Taxonomy refs (TaxIDs): 197Reference(s) to other database(s): GTC:G86373MG, GlycomeDB:
37413
Show glycosyltransferases
There is only one chemically distinct structure:
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