Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Acinetobacter baumannii [ICD11:
XN8LS 
]
The structure was elucidated in this paperNCBI PubMed ID: 28900250Publication DOI: 10.1038/s41598-017-11166-4Journal NLM ID: 101563288Publisher: London: Nature Publishing Group
Correspondence: decastro
unina.it; ruth.hall
sydney.edu.au
Institutions: Institute of Health and Biomedical Innovation, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Department of Chemical Sciences, University of Napoli, Naples, Italy, Saw Swee Hock School of Public Health, National University of Singapore, Singapore, Singapore, Department of Infectious Diseases, Tan Tock Seng Hospital, Singapore, Singapore, Department of Agricultural Sciences, University of Napoli, Naples, Italy
Nonulosonic acids are found in the surface polysaccharides of many bacterial species and are often implicated in pathogenesis. Here, the structure of a novel 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acid recovered from the capsular polysaccharide of a multiply antibiotic resistant Acinetobacter baumannii isolate was determined. The isolate carries a sugar synthesis module that differs by only a single gene from the module for the synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-L-altro-non-2-ulosonic acid or 5,7-di-N-acetylacinetaminic acid, recently discovered in the capsule of another A. baumannii isolate. The new monosaccharide is the C8-epimer of acinetaminic acid (8eAci; 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-L-altro-non-2-ulosonic acid) and the C7-epimer of legionaminic acid. This monosaccharide had not previously been detected in a biological sample but had been synthesized chemically.
structure, Acinetobacter baumannii, capsular polysaccharide, nonulosonic acid, 5, 7, 7-diacetamido-3, legionaminic acid, capsule, surface polysaccharide, 7-Di-N-acetyl-8-epiacinetaminic acid, 9-tetradeoxy-D-glycero-L-altro-non-2-ulosonic acid
Structure type: monomer
Location inside paper: fig.1C, table 1
Compound class: CPS
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, DNA sequencing, GC-MS, enzymatic hydrolysis, mild acid hydrolysis, composition analysis, bioinformatic analysis, SEC
Biosynthesis and genetic data: genetic data
Comments, role: 8-epiacinetaminic acid was isolated from the capsular polysaccharide from A. baumannii K73. The NMR solution was not indicated.
Related record ID(s): 12115
NCBI Taxonomy refs (TaxIDs): 470Reference(s) to other database(s): GTC:G75600RU
Show glycosyltransferases
NMR conditions: at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
5 Ac
7 Ac
aX8eAcip ? ? 40.5 68.3 55.0 76.1 53.5 66.5 20.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
5 Ac
7 Ac
aX8eAcip - - 1.86-2.24 3.95 3.84 3.84 3.90 4.45 1.05
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
5 Ac
7 Ac
aX8eAcip 40.5/1.86-2.24 68.3/3.95 55.0/3.84 76.1/3.84 53.5/3.90 66.5/4.45 20.3/1.05
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 5 | Ac | |
| 7 | Ac | |
| | aX8eAcip |
|
| 1.86
2.24 | 3.95 | 3.84 | 3.84 | 3.90 | 4.45 | 1.05 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 5 | Ac | |
| 7 | Ac | |
| | aX8eAcip | ? | ? | 40.5 | 68.3 | 55.0 | 76.1 | 53.5 | 66.5 | 20.3 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":40.5,"l":"3","c":[0,0,225]},{"s":68.3,"l":"4","c":[0,0,225]},{"s":55,"l":"5","c":[0,0,225]},{"s":76.1,"l":"6","c":[0,0,225]},{"s":53.5,"l":"7","c":[0,0,225]},{"s":66.5,"l":"8","c":[0,0,225]},{"s":20.3,"l":"9","c":[0,0,225]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Found 
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