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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: (Brassicaceae)
Associated disease: black rot disease

The structure was elucidated in this paper
NCBI PubMed ID: 17621551
Publication DOI: 10.1177/0968051907079121
Journal NLM ID: 9433350
Publisher: Maney Publishing
Correspondence: oholst

fz-borstel.de
Institutions: Division of Structural Biochemistry, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Borstel, Germany

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

Structure type: oligomer ; 1448.32
Location inside paper: Fig 3., compound 1
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130701,IEDB_135394,IEDB_141807,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_983930,IEDB_983931,SB_192,SB_197,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, ESI-MS, acid hydrolysis, HPAEC, NMR-1D

Related record ID(s): 2705, 2706, 2707
NCBI Taxonomy refs (TaxIDs): 509169
Reference(s) to other database(s): GlycomeDB:37177
Show glycosyltransferases

NMR conditions: in D2O at 330 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
0,6,6,5,4,4,3	aDManp	103.38	71.15	71.49	68.00	74.53	62.12
0,6,6,5,4,4	aDManp	102.23	71.05	78.85	67.07	75.03	62.12
0,6,6,5,4	bDGlcp	102.57	74.31	77.29	77.31	75.87	61.98
0,6,6,5,3	P
0,6,6,5	aDManp	101.02	70.58	73.48	76.09	75.73	61.20
0,6,6	aXKdop	?	101.14	36.07	66.73	76.33	72.92	70.12	64.51
0,6,4	P
0,6	bDGlcpN	104.35	57.17	77.32	74.17	75.48	64.10
0	aDGlcpN	95.63	56.71	74.80	71.05	72.20	69.86
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
0,6,6,5,4,4,3	aDManp	5.150	4.092	3.907	3.671	3.792	3.794-3.913
0,6,6,5,4,4	aDManp	5.289	4.230	3.956	3.803	3.765	3.796-3.929
0,6,6,5,4	bDGlcp	4.641	3.375	3.669	3.610	3.585	3.775-3.929
0,6,6,5,3	P
0,6,6,5	aDManp	5.121	4.128	4.584	4.110	4.140	3.834-3.986
0,6,6	aXKdop	-	-	1.887-2.102	4.182	4.227	3.867	4.056	3.778-3.936
0,6,4	P
0,6	bDGlcpN	4.437	2.738	3.605	3.734	3.683	3.581-3.730
0	aDGlcpN	5.412	2.695	3.644	3.486	4.071	3.879-4.239
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
0,6,6,5,4,4,3	aDManp	103.38/5.150	71.15/4.092	71.49/3.907	68.00/3.671	74.53/3.792	62.12/3.794-3.913
0,6,6,5,4,4	aDManp	102.23/5.289	71.05/4.230	78.85/3.956	67.07/3.803	75.03/3.765	62.12/3.796-3.929
0,6,6,5,4	bDGlcp	102.57/4.641	74.31/3.375	77.29/3.669	77.31/3.610	75.87/3.585	61.98/3.775-3.929
0,6,6,5,3	P
0,6,6,5	aDManp	101.02/5.121	70.58/4.128	73.48/4.584	76.09/4.110	75.73/4.140	61.20/3.834-3.986
0,6,6	aXKdop			36.07/1.887-2.102	66.73/4.182	76.33/4.227	72.92/3.867	70.12/4.056	64.51/3.778-3.936
0,6,4	P
0,6	bDGlcpN	104.35/4.437	57.17/2.738	77.32/3.605	74.17/3.734	75.48/3.683	64.10/3.581-3.730
0	aDGlcpN	95.63/5.412	56.71/2.695	74.80/3.644	71.05/3.486	72.20/4.071	69.86/3.879-4.239
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
0,6,6,5,4,4,3	aDManp	5.150	4.092	3.907	3.671	3.792	3.794 3.913
0,6,6,5,4,4	aDManp	5.289	4.230	3.956	3.803	3.765	3.796 3.929
0,6,6,5,4	bDGlcp	4.641	3.375	3.669	3.610	3.585	3.775 3.929
0,6,6,5,3	P
0,6,6,5	aDManp	5.121	4.128	4.584	4.110	4.140	3.834 3.986
0,6,6	aXKdop			1.887 2.102	4.182	4.227	3.867	4.056	3.778 3.936
0,6,4	P
0,6	bDGlcpN	4.437	2.738	3.605	3.734	3.683	3.581 3.730
0	aDGlcpN	5.412	2.695	3.644	3.486	4.071	3.879 4.239
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
0,6,6,5,4,4,3	aDManp	103.38	71.15	71.49	68.00	74.53	62.12
0,6,6,5,4,4	aDManp	102.23	71.05	78.85	67.07	75.03	62.12
0,6,6,5,4	bDGlcp	102.57	74.31	77.29	77.31	75.87	61.98
0,6,6,5,3	P
0,6,6,5	aDManp	101.02	70.58	73.48	76.09	75.73	61.20
0,6,6	aXKdop	?	101.14	36.07	66.73	76.33	72.92	70.12	64.51
0,6,4	P
0,6	bDGlcpN	104.35	57.17	77.32	74.17	75.48	64.10
0	aDGlcpN	95.63	56.71	74.80	71.05	72.20	69.86
	P

The spectrum also has 1 signal at unknown position (not plotted).

There is only one chemically distinct structure:

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](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

SVG MW SMILES 3D mol Ionize