Structure and serological characterization of 5,7-diamino-3,5,7,9-tetradeoxy-non-2-ulosonic acid isolated from lipopolysaccharides of Vibrio parahaemolyticus O2 and O-untypable strain KX-V212

Identification of a novel sugar 5,7-diacetamido-8-amino-3,5,7,8,9-pentadeoxy-d-glycero-d-galacto-non-2-ulosonic acid present in the lipooligosaccharide of Vibrio parahaemolyticus O3:K6

“…Relatively large J 4,5 and J 5,6 coupling constants of 10.7 Hz and 10.9 Hz, respectively, confirmed the axial orientation of the pyranose ring protons H-4, H-5 and H-6, which could be due to D-galacto or L-altro configuration [8,20]. were observed [16].…”

“…Although in most cases, the amino groups are substituted with acetyl groups, different N-substitutions are also observed. To mention a few, 5-acetamido-7-(N-acetyl-D-alanyl)-amido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonic acid has been found in O-untypable strain KX-V212 [8], 5-acetamido-3,5,7,9-tetradeoxy-7-[(R)-3-hydroxybutyramido]-L-glycero-L-manno-nonulosonic acid [27] and 5-acetamido-3,5,7, 9-tetradeoxy-7-formamido-L-glycero-L-manno-nonulosonic acid [28] has been reported as constituent sugar of the LPSs of P. aeruginosa O10 and O5 respectively. A novel representative of NonlA such as 5,7-diamino-5,7,9-trideoxy-non-2-ulosonic acid [29] from phytopathogenic Pseudomonas lipopolysaccharide has also been reported.…”

“…The structural variation thus, resides mainly in the oligosaccharide portion of the LOSs. Similar types of LOSs are also found in some parahaemolyticus O2 has been reported to contain 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonic acid [7], where as, a O-untypable strain KX-V212 contains 5-acetamido-7-(N-acetyl-D-alanyl)amido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonic acid [8]. The chemical structure of the lipooligosaccharide of V. parahaemolyticus O2 [7] and V. parahaemolyticus Ountypable strain KX-V212 [9] have been established, recently.…”

“…

A novel sugar,5,5,7,8,, has been identified as a component of the oligosaccharide (OS) isolated from the lipooligosaccharide (LOS) of the emerging strain of Vibrio parahaemolyticus O3:K6 associated with a global pandemic. In the present study we report the identification and characterization of this novel sugar present in the OS of V. parahaemolyticus O3:K6, using chemical analysis, NMR spectroscopy and mass spectrometry.

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A new approach to the synthesis of legionaminic acid analogues

“…3 Other pathogenic species from which legionaminic acid and its derivatives have been isolated include Acinetobacter, [4][5][6][7] Pseudomonas, 4,8,9 Salmonella, 10 Campylobacter, 11,12 Escherichia, [13][14][15] and Vibrio. 4,[16][17][18][19] Given the importance of these nonulosonic acids within a range of human pathogenic bacteria, there is much interest in better understanding their role in pathogenesis and recognition events. However, the structural complexity of these sugars that makes them such attractive biological probes, also makes the synthesis of these sugars quite difficult.…”