A neutral polysaccharide was obtained by hot phenol-water extraction of biomass from Campylobacter jejuni 176.83 and subsequently separated from acid-liberated core oligosaccharide of lipopolysaccharide by sequential GPC on Bio-Gel P6 and TSK-40 columns. All sugar components of the trisaccharide repeating unit of the polysaccharide were found to be of the furanose ring form. The major trisaccharide contained β-L-arabinose, 6-deoxy-β-D-altro-heptose (β-D-6d-altHep) and 6-deoxy-β-L-altrose (β-L-6d-Alt), whereas in the minor trisaccharide the β-L-6d-Alt is replaced by its C-5 epimer α-D-Fuc. On the basis of 1H and 13C NMR spectroscopic studies, including 2D ROESY, HMQC and HMQC-TOCSY experiments, the following structures of the repeating units were established: [formula: see text]

Campylobacter jejuni, L-Arabinose, O41 polysaccharide structure, 6-deoxy-D-altro-heptose, 6-Deoxy-L-altrose, D-fucose

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
2,2	bLAraf	104.8	87.0	76.55	83.5	62.45
2	bD6daltHepf	102.35	91.6	72.0	85.25	69.0	34.35	59.85
	bL6dAltf	99.85	85.9	75.2	86.2	70.05	19.6


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
2,2	bLAraf	5.195	4.34	4.06	4.12	3.74-3.90
2	bD6daltHepf	5.38	4.30	4.405	3.90	3.96	1.70-1.81	3.73-3.78
	bL6dAltf	5.185	4.19	4.34	3.71	3.89	1.27


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7
2,2	bLAraf	104.8/5.195	87.0/4.34	76.55/4.06	83.5/4.12	62.45/3.74-3.90
2	bD6daltHepf	102.35/5.38	91.6/4.30	72.0/4.405	85.25/3.90	69.0/3.96	34.35/1.70-1.81	59.85/3.73-3.78
	bL6dAltf	99.85/5.185	85.9/4.19	75.2/4.34	86.2/3.71	70.05/3.89	19.6/1.27

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

*O[C@H]1[C@@H](O[C@@H]2[C@H](O[C@H]3[C@@H](*)O[C@@H]([C@H](C)O)[C@@H]3O)O[C@H]([C@H](O)CCO)[C@H]2O)O[C@@H](CO)[C@@H]1O

454.425 g/mol (C₁₈H₃₀R₂O₁₃, R = next and previous repeats, not counted in mol weight)