The structure was elucidated in this paper NCBI PubMed ID:17371878 Journal NLM ID:2985121R Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology Correspondence: susan.logannrc-cnrc.gc.ca; evelyn.soonrc-cnrc.gc.ca Institutions: National Research Council, Institute for Biological Sciences, Ottawa, Ontario, Canada
Glycosylation of Campylobacter flagellin is required for the biogenesis of a functional flagella filament. Recently, we used a targeted metabolomics approach using mass spectrometry and NMR to identify changes in the metabolic profile of wild type and mutants in the flagellar glycosylation locus, characterize novel metabolites, and assign function to genes to define the pseudaminic acid biosynthetic pathway in Campylobacter jejuni 81-176 (McNally, D. J., Hui, J. P., Aubry, A. J., Mui, K. K., Guerry, P., Brisson, J. R., Logan, S. M., and Soo, E. C. (2006) J. Biol. Chem. 281, 18489-18498). In this study, we use a similar approach to further define the glycome and metabolomic complement of nucleotide-activated sugars in Campylobacter coli VC167. Herein we demonstrate that, in addition to CMP-pseudaminic acid, C. coli VC167 also produces two structurally distinct nucleotide-activated nonulosonate sugars that were observed as negative ions at m/z 637 and m/z 651 (CMP-315 and CMP-329). Hydrophilic interaction liquid chromatography-mass spectrometry yielded suitable amounts of the pure sugar nucleotides for NMR spectroscopy using a cold probe. Structural analysis in conjunction with molecular modeling identified the sugar moieties as acetamidino and N-methylacetimidoyl derivatives of legionaminic acid (Leg5Am7Ac and Leg5AmNMe7Ac). Targeted metabolomic analyses of isogenic mutants established a role for the ptmA-F genes and defined two new ptm genes in this locus as legionaminic acid biosynthetic enzymes. This is the first report of legionaminic acid in Campylobacter sp. and the first report of legionaminic acid derivatives as modifications on a protein
Structure type: monomer Location inside paper: p. 14469, table 3, III Trivial name: 5-acetamidino-7-acetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-nonulosonic (Leg5Am7Ac)
Methods: 13C NMR, 1H NMR, NMR-2D, MD simulations, NMR-1D, genetic methods, biochemical methods, biosynthetic methods, CE-ESI-MS, LC-MS Biosynthesis and genetic data: genetic data, biochemical data 3D data: molecular modeling
Related record ID(s): 21505, 21874, 21875, 21877 NCBI Taxonomy refs (TaxIDs):195 Reference(s) to other database(s): GlycomeDB:35005 Show glycosyltransferases
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