Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: pneumonia [ICD11:
CA40 
];
urinary tract infections (UTI) [ICD11:
GC08 ];
septicemia [ICD11:
MA15.Y ];
infection due to Acinetobacter baumannii [ICD11:
XN8LS ]
The structure was elucidated in this paperNCBI PubMed ID: 27509201Publication DOI: 10.1016/j.carres.2016.07.016Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: C. De Castro <decastro
unina.it>
Institutions: School of Molecular Bioscience, University of Sydney, Australia, Institute of Health and Biomedical Innovation, Queensland University of Technology, Australia, Department of Chemical Sciences, University of Napoli, Italy, Department of Agricultural Sciences, University of Napoli, Italy
The structure of the K4 capsular polysaccharide (CPS) from a multiply antibiotic resistant Acinetobacter baumannii isolate D78 was elucidated by chemical and spectroscopical analysis. The K4 repeating unit is composed entirely by aminosugars and the trisaccharide repeating unit of the backbone polysaccharide is branched with a terminal N-acetyl-galactosamine capped with pyruvate as cyclic acetal. Each residue is in the pyranose form, alpha configured at the anomeric center, and has the D absolute configuration. The genes responsible for the synthesis of the K4 repeat unit and its polymerization and export are found in the capsule locus KL4 present in D78. The pyruvate acetal addition to galactosamine is formed by Ptr1, a novel pyruvate transferase, encoded at this locus.
NMR, structure, Acinetobacter baumannii, pyruvate acetal, CPS, Pyruvate transferase
Structure type: polymer chemical repeating unit
Location inside paper: p.13, fig.2
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_885822
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, acid hydrolysis, mild acid hydrolysis, NMR-1D, peracetylation, SEC
NCBI Taxonomy refs (TaxIDs): 470
Show glycosyltransferases
NMR conditions: in D2O at 318 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,4,2 Ac ? 23.1-23.7
3,4,6,6 40%xRPyr 176.0 101.0 26.0
3,4,6,2 Ac ? 23.1-23.7
3,4,6 aDGalpN 98.2 50.7 66.8 71.9 63.4 66.2
3,4 aDGalpN 100.4 51.1 67.8 76.3 70.4 64.0
3,2 Ac ? 23.1-23.7
3 aDGalpNA 100.1 50.9 67.9 79.9 72.2 173.4
2 Ac ? 23.1-23.7
aDQuipN 98.9 54.0 80.0 77.5 69.1 17.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,4,2 Ac - 1.99-2.09
3,4,6,6 40%xRPyr - - 1.51
3,4,6,2 Ac - 1.99-2.09
3,4,6 aDGalpN 4.72 4.23 3.97 4.17 3.63 3.89-3.91
3,4 aDGalpN 4.96 4.26 4.12 4.11 4.46 3.33-3.70
3,2 Ac - 1.99-2.09
3 aDGalpNA 5.30 4.19 3.97 4.33 4.31 -
2 Ac - 1.99-2.09
aDQuipN 4.79 4.04 3.91 3.39 4.29 1.24
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,4,2 Ac 23.1-23.7/1.99-2.09
3,4,6,6 40%xRPyr 26.0/1.51
3,4,6,2 Ac 23.1-23.7/1.99-2.09
3,4,6 aDGalpN 98.2/4.72 50.7/4.23 66.8/3.97 71.9/4.17 63.4/3.63 66.2/3.89-3.91
3,4 aDGalpN 100.4/4.96 51.1/4.26 67.8/4.12 76.3/4.11 70.4/4.46 64.0/3.33-3.70
3,2 Ac 23.1-23.7/1.99-2.09
3 aDGalpNA 100.1/5.30 50.9/4.19 67.9/3.97 79.9/4.33 72.2/4.31
2 Ac 23.1-23.7/1.99-2.09
aDQuipN 98.9/4.79 54.0/4.04 80.0/3.91 77.5/3.39 69.1/4.29 17.4/1.24
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,4,2 | Ac |
| 1.99
2.09 | |
| 3,4,6,6 | 40%xRPyr |
|
| 1.51 | |
| 3,4,6,2 | Ac |
| 1.99
2.09 | |
| 3,4,6 | aDGalpN | 4.72 | 4.23 | 3.97 | 4.17 | 3.63 | 3.89
3.91 |
| 3,4 | aDGalpN | 4.96 | 4.26 | 4.12 | 4.11 | 4.46 | 3.33
3.70 |
| 3,2 | Ac |
| 1.99
2.09 | |
| 3 | aDGalpNA | 5.30 | 4.19 | 3.97 | 4.33 | 4.31 |
|
| 2 | Ac |
| 1.99
2.09 | |
| | aDQuipN | 4.79 | 4.04 | 3.91 | 3.39 | 4.29 | 1.24 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,4,2 | Ac | ? | 23.1
23.7 | |
| 3,4,6,6 | 40%xRPyr | 176.0 | 101.0 | 26.0 | |
| 3,4,6,2 | Ac | ? | 23.1
23.7 | |
| 3,4,6 | aDGalpN | 98.2 | 50.7 | 66.8 | 71.9 | 63.4 | 66.2 |
| 3,4 | aDGalpN | 100.4 | 51.1 | 67.8 | 76.3 | 70.4 | 64.0 |
| 3,2 | Ac | ? | 23.1
23.7 | |
| 3 | aDGalpNA | 100.1 | 50.9 | 67.9 | 79.9 | 72.2 | 173.4 |
| 2 | Ac | ? | 23.1
23.7 | |
| | aDQuipN | 98.9 | 54.0 | 80.0 | 77.5 | 69.1 | 17.4 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":23.4,"l":"2","c":[0,0,0]},{"s":176,"l":"1","c":[0,0,225]},{"s":101,"l":"2","c":[0,0,225]},{"s":26,"l":"3","c":[0,0,225]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":98.2,"l":"1","c":[230,0,30]},{"s":50.7,"l":"2","c":[230,0,30]},{"s":66.8,"l":"3","c":[230,0,30]},{"s":71.9,"l":"4","c":[230,0,30]},{"s":63.4,"l":"5","c":[230,0,30]},{"s":66.2,"l":"6","c":[230,0,30]},{"s":100.4,"l":"1","c":[0,165,0]},{"s":51.1,"l":"2","c":[0,165,0]},{"s":67.8,"l":"3","c":[0,165,0]},{"s":76.3,"l":"4","c":[0,165,0]},{"s":70.4,"l":"5","c":[0,165,0]},{"s":64,"l":"6","c":[0,165,0]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":100.1,"l":"1","c":[120,0,225]},{"s":50.9,"l":"2","c":[120,0,225]},{"s":67.9,"l":"3","c":[120,0,225]},{"s":79.9,"l":"4","c":[120,0,225]},{"s":72.2,"l":"5","c":[120,0,225]},{"s":173.4,"l":"6","c":[120,0,225]},{"s":23.4,"l":"2","c":[0,0,0]},{"s":98.9,"l":"1","c":[0,192,255]},{"s":54,"l":"2","c":[0,192,255]},{"s":80,"l":"3","c":[0,192,255]},{"s":77.5,"l":"4","c":[0,192,255]},{"s":69.1,"l":"5","c":[0,192,255]},{"s":17.4,"l":"6","c":[0,192,255]}])
The spectrum also has 4 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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