Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: (Brassicaceae)
Associated disease: black rot disease
The structure was elucidated in this paperNCBI PubMed ID: 17621551Publication DOI: 10.1177/0968051907079121Journal NLM ID: 9433350Publisher: 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 ; 1124.22
Location inside paper: Fig 3., compound 2
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_983930,IEDB_983931,SB_192,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): 2704, 2706, 2707
NCBI Taxonomy refs (TaxIDs): 509169Reference(s) to other database(s): GlycomeDB:
27779
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 bDGlcp 102.77 74.21 76.89 70.97 77.17 61.86
0,6,6,5,3 P
0,6,6,5 aDManp 100.85 70.64 73.66 76.30 75.84 61.23
0,6,6 aXKdop ? 101.04 36.18 66.75 76.26 72.77 70.13 64.55
0,6,4 P
0,6 bDGlcpN 104.32 57.22 77.21 74.16 75.55 64.14
0 aDGlcpN 95.60 56.72 74.80 71.11 72.20 69.88
P
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
0,6,6,5,4 bDGlcp 4.633 3.362 3.510 3.396 3.489 3.735-3.909
0,6,6,5,3 P
0,6,6,5 aDManp 5.115 4.095 4.586 4.114 4.142 3.835-3.980
0,6,6 aXKdop - - 1.883-2.099 4.177 4.226 3.853 4.042 3.775-3.940
0,6,4 P
0,6 bDGlcpN 4.440 2.739 3.603 3.737 3.681 3.570-3.714
0 aDGlcpN 5.407 2.697 3.646 3.486 4.070 3.869-4.240
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 bDGlcp 102.77/4.633 74.21/3.362 76.89/3.510 70.97/3.396 77.17/3.489 61.86/3.735-3.909
0,6,6,5,3 P
0,6,6,5 aDManp 100.85/5.115 70.64/4.095 73.66/4.586 76.30/4.114 75.84/4.142 61.23/3.835-3.980
0,6,6 aXKdop 36.18/1.883-2.099 66.75/4.177 76.26/4.226 72.77/3.853 70.13/4.042 64.55/3.775-3.940
0,6,4 P
0,6 bDGlcpN 104.32/4.440 57.22/2.739 77.21/3.603 74.16/3.737 75.55/3.681 64.14/3.570-3.714
0 aDGlcpN 95.60/5.407 56.72/2.697 74.80/3.646 71.11/3.486 72.20/4.070 69.88/3.869-4.240
P
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 0,6,6,5,4 | bDGlcp | 4.633 | 3.362 | 3.510 | 3.396 | 3.489 | 3.735
3.909 | |
| 0,6,6,5,3 | P | |
| 0,6,6,5 | aDManp | 5.115 | 4.095 | 4.586 | 4.114 | 4.142 | 3.835
3.980 | |
| 0,6,6 | aXKdop |
|
| 1.883
2.099 | 4.177 | 4.226 | 3.853 | 4.042 | 3.775
3.940 |
| 0,6,4 | P | |
| 0,6 | bDGlcpN | 4.440 | 2.739 | 3.603 | 3.737 | 3.681 | 3.570
3.714 | |
| 0 | aDGlcpN | 5.407 | 2.697 | 3.646 | 3.486 | 4.070 | 3.869
4.240 | |
| | P | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 0,6,6,5,4 | bDGlcp | 102.77 | 74.21 | 76.89 | 70.97 | 77.17 | 61.86 | |
| 0,6,6,5,3 | P | |
| 0,6,6,5 | aDManp | 100.85 | 70.64 | 73.66 | 76.30 | 75.84 | 61.23 | |
| 0,6,6 | aXKdop | ? | 101.04 | 36.18 | 66.75 | 76.26 | 72.77 | 70.13 | 64.55 |
| 0,6,4 | P | |
| 0,6 | bDGlcpN | 104.32 | 57.22 | 77.21 | 74.16 | 75.55 | 64.14 | |
| 0 | aDGlcpN | 95.60 | 56.72 | 74.80 | 71.11 | 72.20 | 69.88 | |
| | P | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":102.77,"l":"1","c":[0,0,225]},{"s":74.21,"l":"2","c":[0,0,225]},{"s":76.89,"l":"3","c":[0,0,225]},{"s":70.97,"l":"4","c":[0,0,225]},{"s":77.17,"l":"5","c":[0,0,225]},{"s":61.86,"l":"6","c":[0,0,225]},{"s":100.85,"l":"1","c":[230,0,30]},{"s":70.64,"l":"2","c":[230,0,30]},{"s":73.66,"l":"3","c":[230,0,30]},{"s":76.3,"l":"4","c":[230,0,30]},{"s":75.84,"l":"5","c":[230,0,30]},{"s":61.23,"l":"6","c":[230,0,30]},{"s":101.04,"l":"2","c":[0,165,0]},{"s":36.18,"l":"3","c":[0,165,0]},{"s":66.75,"l":"4","c":[0,165,0]},{"s":76.26,"l":"5","c":[0,165,0]},{"s":72.77,"l":"6","c":[0,165,0]},{"s":70.13,"l":"7","c":[0,165,0]},{"s":64.55,"l":"8","c":[0,165,0]},{"s":104.32,"l":"1","c":[120,0,225]},{"s":57.22,"l":"2","c":[120,0,225]},{"s":77.21,"l":"3","c":[120,0,225]},{"s":74.16,"l":"4","c":[120,0,225]},{"s":75.55,"l":"5","c":[120,0,225]},{"s":64.14,"l":"6","c":[120,0,225]},{"s":95.6,"l":"1","c":[0,192,255]},{"s":56.72,"l":"2","c":[0,192,255]},{"s":74.8,"l":"3","c":[0,192,255]},{"s":71.11,"l":"4","c":[0,192,255]},{"s":72.2,"l":"5","c":[0,192,255]},{"s":69.88,"l":"6","c":[0,192,255]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
