Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Acinetobacter baumannii [ICD11:
XN8LS 
]
The structure was elucidated in this paperNCBI PubMed ID: 9774431Publication DOI: 10.1074/jbc.273.43.28122Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: oholst
fz-borstel.de
Institutions: Division of Medical and Biochemical Microbiology, Research Center Borstel, Center for Medicine and Biosciences, D-23845 Borstel, Germany, Department of Chemistry, Carlsberg Laboratory, DK-2500 Valby, Denmark, Department of Mass Spectrometry, Bijvoet Center for Biomolecular Research, Utrecht University,NL-3584 CA Utrecht, The Netherlands
For the first time, the tetrasaccharide Kdo a2→5 Kdo a2→5 (Kdo a2→4)Kdo (Kdo is 3-deoxy-Dmanno-oct-2-ulopyranosonic acid) has been identified in a bacterial lipopolysaccharide (LPS), i.e. in the core region of LPS from Acinetobacter baumannii NCTC 10303. The LPS was analyzed using compositional analysis, mass spectrometry, and NMR spectroscopy. The disaccharide DGlcpN b1→6 DGlcpN, phosphorylated at O-1 and O-4', was identified as the carbohydrate backbone of the lipid A. The Kdo tetrasaccharide is attached to O-6' of this disaccharide and is further substituted by short L-rhamnoglycans of varying length and by the disaccharide DGlcpNAc a1→4 DGlcpNA (GlcpNA, 2-amino-2-deoxy-glucopyranosuronic acid). The core region is not substituted by phosphate residues and represents a novel core type of bacterial LPS. The complete carbohydrate backbone of the LPS is shown in Structure I as follows: [see formula in text] where Rha is rhamnose. Except were indicated, monosaccharides possess the D-configuration. Sugars marked with an asterisk are present in non-stoichiometric amounts.
LPS, structure, core, acid, Acinetobacter, Acinetobacter baumannii, 3-deoxy-D-manno-oct-2-ulopyranosonic
Structure type: oligomer
Location inside paper: fig.1, oligosaccharide 6
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_135394,IEDB_141807,IEDB_150908,IEDB_151531
Methods: NMR-2D, NMR, MS, composition analysis
3D data: 3D data
Related record ID(s): 343, 5528, 5688, 5689, 5690, 5691, 5692, 5694
NCBI Taxonomy refs (TaxIDs): 470Reference(s) to other database(s): GlycomeDB:
26763
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
0,6,6,4 aXKdop ? ? 34.8 65.9 67.2 72.4 71.5 63.4
0,6,6,5,4,4 aDGlcpN 97.2 55.0 71.8 70.0 72.0 60.5
0,6,6,5,4 aDGlcpNA 94.4 55.0 73.8 76.6 73.3 ?
0,6,6,5 aXKdop ? ? 33.4 70.0 63.5 72.9 71.0 64.2
0,6,6 aXKdop ? ? 34.8 72.9 68.0 73.3 70.2 64.2
0,6,4 P
0,6 bDGlcpN 101.6 56.0 73.4 73.8-74.7 73.8-74.7 63.0
0 aDGlcpN 91.8 55.3 70.8 70.0 72.4 70.5
P
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
0,6,6,4 aXKdop - - 1.765-1.936 4.115 4.006 3.636 3.949 3.722-3.965
0,6,6,5,4,4 aDGlcpN 5.585 2.998 3.728 3.386 3.745 3.80-3.80
0,6,6,5,4 aDGlcpNA 5.206 3.008 3.968 3.796 4.108 -
0,6,6,5 aXKdop - - 2.017-2.428 4.428 4.273 4.481 4.009 3.829-3.943
0,6,6 aXKdop - - 1.973-2.147 3.975 4.407 3.604 3.750 3.556-3.857
0,6,4 P
0,6 bDGlcpN 4.752 2.983 3.792 3.684 3.684 3.393-3.698
0 aDGlcpN 5.594 3.278 3.841 3.665 4.139 3.716-4.273
P
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
0,6,6,4 aXKdop 34.8/1.765-1.936 65.9/4.115 67.2/4.006 72.4/3.636 71.5/3.949 63.4/3.722-3.965
0,6,6,5,4,4 aDGlcpN 97.2/5.585 55.0/2.998 71.8/3.728 70.0/3.386 72.0/3.745 60.5/3.80-3.80
0,6,6,5,4 aDGlcpNA 94.4/5.206 55.0/3.008 73.8/3.968 76.6/3.796 73.3/4.108
0,6,6,5 aXKdop 33.4/2.017-2.428 70.0/4.428 63.5/4.273 72.9/4.481 71.0/4.009 64.2/3.829-3.943
0,6,6 aXKdop 34.8/1.973-2.147 72.9/3.975 68.0/4.407 73.3/3.604 70.2/3.750 64.2/3.556-3.857
0,6,4 P
0,6 bDGlcpN 101.6/4.752 56.0/2.983 73.4/3.792 73.8-74.7/3.684 73.8-74.7/3.684 63.0/3.393-3.698
0 aDGlcpN 91.8/5.594 55.3/3.278 70.8/3.841 70.0/3.665 72.4/4.139 70.5/3.716-4.273
P
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 0,6,6,4 | aXKdop |
|
| 1.765
1.936 | 4.115 | 4.006 | 3.636 | 3.949 | 3.722
3.965 |
| 0,6,6,5,4,4 | aDGlcpN | 5.585 | 2.998 | 3.728 | 3.386 | 3.745 | 3.80
3.80 | |
| 0,6,6,5,4 | aDGlcpNA | 5.206 | 3.008 | 3.968 | 3.796 | 4.108 |
| |
| 0,6,6,5 | aXKdop |
|
| 2.017
2.428 | 4.428 | 4.273 | 4.481 | 4.009 | 3.829
3.943 |
| 0,6,6 | aXKdop |
|
| 1.973
2.147 | 3.975 | 4.407 | 3.604 | 3.750 | 3.556
3.857 |
| 0,6,4 | P | |
| 0,6 | bDGlcpN | 4.752 | 2.983 | 3.792 | 3.684 | 3.684 | 3.393
3.698 | |
| 0 | aDGlcpN | 5.594 | 3.278 | 3.841 | 3.665 | 4.139 | 3.716
4.273 | |
| | P | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 0,6,6,4 | aXKdop | ? | ? | 34.8 | 65.9 | 67.2 | 72.4 | 71.5 | 63.4 |
| 0,6,6,5,4,4 | aDGlcpN | 97.2 | 55.0 | 71.8 | 70.0 | 72.0 | 60.5 | |
| 0,6,6,5,4 | aDGlcpNA | 94.4 | 55.0 | 73.8 | 76.6 | 73.3 | ? | |
| 0,6,6,5 | aXKdop | ? | ? | 33.4 | 70.0 | 63.5 | 72.9 | 71.0 | 64.2 |
| 0,6,6 | aXKdop | ? | ? | 34.8 | 72.9 | 68.0 | 73.3 | 70.2 | 64.2 |
| 0,6,4 | P | |
| 0,6 | bDGlcpN | 101.6 | 56.0 | 73.4 | 73.8
74.7 | 73.8
74.7 | 63.0 | |
| 0 | aDGlcpN | 91.8 | 55.3 | 70.8 | 70.0 | 72.4 | 70.5 | |
| | P | |
|
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The spectrum also has 7 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
