The rough-type lipopolysaccharide (LPS) of the phytopathogenic bacterium Xanthomonas campestris pv. campestris B 100 was isolated utilizing the hot phenol-water method and successively de-acylated by treatment with hydrazine and hot potassium hydroxide. Four compounds were separated by preparative high-performance anion-exchange chromatography and studied by sugar analysis and by 1D and 2D homonuclear and heteronuclear (1)H-, (13)C- and (31)P-NMR spectroscopy as well as ESI FT-MS. The two main products were a heptasaccharide and a pentasaccharide of the structures α-D-Manp-(1→3)-α-D-Manp-(1→4)-β-D-Glcp-(1→4)-α-D-Manp-3P-(1→5)-α-Kdo-(2→6)-β-D-GlcpN-4P-(1→6)-α-D-GlcpN-1P (1) and β-D-Glcp-(1→4)-α-D-Manp-3P-(1→5)-α-Kdo-(2→6)-β-D-GlcpN-4P-(1→6)-α-D-GlcpN-1P (2), respectively. The products in smaller amounts were a heptasaccharide and pentasaccharide possessing the above structures plus a phosphate group at C-4 of the Kdo residue (compounds 3 and 4). Both, heptasaccharide 1 and pentasaccharide 2 were able to induce an oxidative burst in cell cultures of the non-host plant tobacco

lipopolysaccharides, NMR spectroscopy, structural analysis, ESI FT-MS, Xanthomonas campestris pv. campestris, oxidative burst

13C NMR data:
missing...
1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
0,6,6,5,4	bDGlcp	4.591	3.367	3.495	3.370	3.464	3.717-3.909
0,6,6,5,3	P
0,6,6,5	aDManp	5.228	4.305	4.494	3.989	3.973	3.851-3.982
0,6,6,4	P
0,6,6	aXKdop	-	-	2.024-2.245	4.474	4.329	3.862	4.011	3.776-3.920
0,6,4	P
0,6	bDGlcpN	4.429	2.715	3.598	3.721	3.680	3.561-3.758
0	aDGlcpN	5.402	2.703	3.627	3.429	4.067	3.806-4.337
	P

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

N[C@H]1[C@@H](OP(=O)(O)O)O[C@H](CO[C@@H]2O[C@H](CO[C@]3(C(=O)O)C[C@@H](OP(=O)(O)O)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](OP(=O)(O)O)[C@@H]4O)[C@@H]([C@H](O)CO)O3)[C@@H](OP(=O)(O)O)[C@H](O)[C@H]2N)[C@@H](O)[C@@H]1O

1204.704 g/mol (C₃₂H₆₀N₂O₃₈P₄)