Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: urinary tract infections (UTI) [ICD11:
GC08 
];
meningitis [ICD11:
1D01 ];
septicemia [ICD11:
MA15.Y ];
infection due to Acinetobacter baumannii [ICD11:
XN8LS ]
The structure was elucidated in this paperPublication DOI: 10.1002/ejoc.200901396Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: decastro
unina.it
Institutions: Department of Organic Chemistry and Biochemistry, University of Napoli Federico II - Complesso Universitario Monte Sant’Angelo, Via Cinthia 4, 80126 Napoli, Italy
Acinetobacter baumannii is a pathogenic organism that posesses a serious health threat because of the occurrence of the large number of (multi)drug-resistant strains. It can persist for prolonged periods in the hospital environment, infecting debilitated or immune-compromised patients. In this context, the endotoxin portion of the lipopolysaccharide, the lipid A, plays an important role in the pathogenesis of this bacterium, because it triggers the innate immune response and contributes to the inflammation state of the patient. In this study, the complete structure of the lipooligosaccharide has been determined. The saccharide backbone of the molecule was disclosed through chemical and spectroscopic analysis, whereas the lipid A moiety required detailed MS spectrometry and chemical investigations. The oligosaccharide backbone was found to be similar to that of A. baumannii ATCC 19606, although the LOS from the SMAL strain presented an enhanced zwitterionic character. The lipid A moiety comprises a heterogeneous and complex mixture of molecules: it possesses a conserved diphosphorylated disaccharide backbone substituted by three to seven fatty acids. The hexaacylated species appeared as the most abundant, and its chemical features, namely the number and the types of fatty acids, indicates its potential endotoxic activity.
Acinetobacter baumannii, NMR spectroscopy, structure elucidation, mass spectrometry, glycolipids
Structure type: oligomer
Location inside paper: p.1346, fig.1, 1, table S2
Aglycon: lipid A
Compound class: core oligosaccharide, LOS
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_137473,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, GC-MS, deacylation, acid hydrolysis, alkaline degradation, ESI-ICR-MS, chemical methods
Related record ID(s): 28699, 28700, 28701
NCBI Taxonomy refs (TaxIDs): 470Reference(s) to other database(s): GTC:G87252TX
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
4 aXKdop
5,4,3,4,4,2 aDGlcp 98.6 72.6 74.0 71.0 72.9 61.4
5,4,3,4,4 bDGlcp 102.7 77.3 75.5 70.8 74.0 61.9
5,4,3,4 bDGlcp 103.6 74.4 76.2 79.4 75.0 61.8
5,4,3 bDGlcp 104.2 73.8 75.2 76.1 74.0 61.8
5,4,2 Ac
5,4,4 aDGalpN 96.6 52.2 67.5 68.9 72.3 61.7
5,4 aDGlcpNA 95.9 54.3 78.2 75.3 74.4 176.1
5,7 bDGlcpN 99.2 57.1 73.5 71.2 77.5 61.8
5 aXKdop 178.8 97.5 34.0 72.1 64.0 71.2 77.8 61.5
aXKdop
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
4 aXKdop
5,4,3,4,4,2 aDGlcp 5.37 3.52 3.75 3.45 4.06 3.75-3.80
5,4,3,4,4 bDGlcp 4.66 3.51 3.59 3.46 3.75 3.70-3.92
5,4,3,4 bDGlcp 4.54 3.35 3.66 3.76 3.66 3.87-4.00
5,4,3 bDGlcp 4.67 3.36 3.62 3.57 3.74 3.95-3.95
5,4,2 Ac
5,4,4 aDGalpN 5.74 3.54 4.00 4.02 3.96 3.70-3.90
5,4 aDGlcpNA 5.06 4.27 4.34 3.98 4.11 -
5,7 bDGlcpN 4.95 3.12 3.68 3.47 3.53 3.93-3.93
5 aXKdop - - 1.95-2.16 4.13 4.32 3.92 4.12 3.80-3.80
aXKdop
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
4 aXKdop
5,4,3,4,4,2 aDGlcp 98.6/5.37 72.6/3.52 74.0/3.75 71.0/3.45 72.9/4.06 61.4/3.75-3.80
5,4,3,4,4 bDGlcp 102.7/4.66 77.3/3.51 75.5/3.59 70.8/3.46 74.0/3.75 61.9/3.70-3.92
5,4,3,4 bDGlcp 103.6/4.54 74.4/3.35 76.2/3.66 79.4/3.76 75.0/3.66 61.8/3.87-4.00
5,4,3 bDGlcp 104.2/4.67 73.8/3.36 75.2/3.62 76.1/3.57 74.0/3.74 61.8/3.95-3.95
5,4,2 Ac
5,4,4 aDGalpN 96.6/5.74 52.2/3.54 67.5/4.00 68.9/4.02 72.3/3.96 61.7/3.70-3.90
5,4 aDGlcpNA 95.9/5.06 54.3/4.27 78.2/4.34 75.3/3.98 74.4/4.11
5,7 bDGlcpN 99.2/4.95 57.1/3.12 73.5/3.68 71.2/3.47 77.5/3.53 61.8/3.93-3.93
5 aXKdop 34.0/1.95-2.16 72.1/4.13 64.0/4.32 71.2/3.92 77.8/4.12 61.5/3.80-3.80
aXKdop
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 4 | aXKdop | |
| 5,4,3,4,4,2 | aDGlcp | 5.37 | 3.52 | 3.75 | 3.45 | 4.06 | 3.75
3.80 | |
| 5,4,3,4,4 | bDGlcp | 4.66 | 3.51 | 3.59 | 3.46 | 3.75 | 3.70
3.92 | |
| 5,4,3,4 | bDGlcp | 4.54 | 3.35 | 3.66 | 3.76 | 3.66 | 3.87
4.00 | |
| 5,4,3 | bDGlcp | 4.67 | 3.36 | 3.62 | 3.57 | 3.74 | 3.95
3.95 | |
| 5,4,2 | Ac | |
| 5,4,4 | aDGalpN | 5.74 | 3.54 | 4.00 | 4.02 | 3.96 | 3.70
3.90 | |
| 5,4 | aDGlcpNA | 5.06 | 4.27 | 4.34 | 3.98 | 4.11 |
| |
| 5,7 | bDGlcpN | 4.95 | 3.12 | 3.68 | 3.47 | 3.53 | 3.93
3.93 | |
| 5 | aXKdop |
|
| 1.95
2.16 | 4.13 | 4.32 | 3.92 | 4.12 | 3.80
3.80 |
| | aXKdop | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 4 | aXKdop | |
| 5,4,3,4,4,2 | aDGlcp | 98.6 | 72.6 | 74.0 | 71.0 | 72.9 | 61.4 | |
| 5,4,3,4,4 | bDGlcp | 102.7 | 77.3 | 75.5 | 70.8 | 74.0 | 61.9 | |
| 5,4,3,4 | bDGlcp | 103.6 | 74.4 | 76.2 | 79.4 | 75.0 | 61.8 | |
| 5,4,3 | bDGlcp | 104.2 | 73.8 | 75.2 | 76.1 | 74.0 | 61.8 | |
| 5,4,2 | Ac | |
| 5,4,4 | aDGalpN | 96.6 | 52.2 | 67.5 | 68.9 | 72.3 | 61.7 | |
| 5,4 | aDGlcpNA | 95.9 | 54.3 | 78.2 | 75.3 | 74.4 | 176.1 | |
| 5,7 | bDGlcpN | 99.2 | 57.1 | 73.5 | 71.2 | 77.5 | 61.8 | |
| 5 | aXKdop | 178.8 | 97.5 | 34.0 | 72.1 | 64.0 | 71.2 | 77.8 | 61.5 |
| | aXKdop | |
|
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
