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
0,6,6,5,4,4,3	aDManp	5.137	4.074	3.894	3.658	3.778	3.796-3.912
0,6,6,5,4,4	aDManp	5.277	4.213	3.938	3.768	3.747	3.796-3.918
0,6,6,5,4	bDGlcp	4.594	3.382	3.657	3.584	3.544	3.747-3.927
0,6,6,5,3	P
0,6,6,5	aDManp	5.228	4.284	4.490	3.980	3.965	3.850-3.969
0,6,6,4	P
0,6,6	aXKdop	-	-	2.018-2.231	4.467	4.322	3.857	4.002	3.769-3.918
0,6,4	P
0,6	bDGlcpN	4.422	2.711	3.590	3.714	3.683	3.576-3.760
0	aDGlcpN	5.401	2.695	3.614	3.402	4.069	3.793-4.349
	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]6O[C@H](CO)[C@@H](O)[C@H](O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O)[C@@H]6O)[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

1528.986 g/mol (C₄₄H₈₀N₂O₄₈P₄)