Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: cystic fibrosis (CF) [ICD11:
CA25 
]
The structure was elucidated in this paperPublication DOI: 10.1002/ejoc.201200047Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: Antonio Molinaro <molinaro
unina.it>
Institutions: Dipartimento di Scienze Chimiche, Università di Napoli“Federico II”, Complesso Universitario Monte S. Angelo,Via Cintia 4, 80126 Napoli, Italy, Centre of Microbial Host Interactions, ITT Dublin,Tallaght, Dublin 24, Ireland, CNR Istituto per la Chimica e la Tecnologia dei Polimeri,Via P. Gaifami 18, 95126 Catania, Italy
This is the first report on the molecular structure of the O-chain of the lipopolysaccharide produced by the emerging and highly virulent clinical isolate Pandoraea pulmonicola strain LMG 18108, an opportunistic human pathogen in cystic fibrosis patients. Monosaccharide analysis and 2D NMR spectroscopy revealed a novel polysaccharide, the structure of which consists of the trisaccharide repeating unit [→2-β-D-Quip3NAcyl-(1→4)-α-D-GalpNAc-(1→3)-α-D-GlcpNAc-1→]n. The quinovosamine residue was found to be linked by a very unusual acyl substituent, a five-membered-ring acyl residue, the 3-hydroxy-2,3-dimethyl-5-oxoprolyl group.
carbohydrates, antigens, NMR spectroscopy, structure elucidation, cystic fibrosis, Pandoraea
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.2247, Fig. 5
Compound class: O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, SDS-PAGE, sugar analysis, MALDI-TOF MS
NCBI Taxonomy refs (TaxIDs): 93221
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7
3,4,3 x?3HO2,3MePro-5-oxo 176.1 72.8 79.7 46.2 180.8 19.5 23.5
3,4 bDQuip3N 105.7 72.7 57.4 74.4 74.6 18.1
3,2 Ac ? 23.4-23.8
3 aDGalpN 99.8 51.1 68.2 79.4 72.6 62.6
2 Ac ? 23.4-23.8
aDGlcpN 95.6 53.0 79.2 72.0 71.8 62.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7
3,4,3 x?3HO2,3MePro-5-oxo - - - 2.25-2.60 - 1.34 1.21
3,4 bDQuip3N 4.56 3.46 3.89 3.10 3.28 1.11
3,2 Ac - 1.78-1.87
3 aDGalpN 5.27 4.06 3.75 4.20 3.99 3.77
2 Ac - 1.78-1.87
aDGlcpN 5.61 3.78 3.42 3.59 3.65 3.61-3.77
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7
3,4,3 x?3HO2,3MePro-5-oxo 46.2/2.25-2.60 19.5/1.34 23.5/1.21
3,4 bDQuip3N 105.7/4.56 72.7/3.46 57.4/3.89 74.4/3.10 74.6/3.28 18.1/1.11
3,2 Ac 23.4-23.8/1.78-1.87
3 aDGalpN 99.8/5.27 51.1/4.06 68.2/3.75 79.4/4.20 72.6/3.99 62.6/3.77
2 Ac 23.4-23.8/1.78-1.87
aDGlcpN 95.6/5.61 53.0/3.78 79.2/3.42 72.0/3.59 71.8/3.65 62.6/3.61-3.77
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 |
|---|
| 3,4,3 | x?3HO2,3MePro-5-oxo |
|
|
| 2.25
2.60 |
| 1.34 | 1.21 |
| 3,4 | bDQuip3N | 4.56 | 3.46 | 3.89 | 3.10 | 3.28 | 1.11 | |
| 3,2 | Ac |
| 1.78
1.87 | |
| 3 | aDGalpN | 5.27 | 4.06 | 3.75 | 4.20 | 3.99 | 3.77 | |
| 2 | Ac |
| 1.78
1.87 | |
| | aDGlcpN | 5.61 | 3.78 | 3.42 | 3.59 | 3.65 | 3.61
3.77 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 |
|---|
| 3,4,3 | x?3HO2,3MePro-5-oxo | 176.1 | 72.8 | 79.7 | 46.2 | 180.8 | 19.5 | 23.5 |
| 3,4 | bDQuip3N | 105.7 | 72.7 | 57.4 | 74.4 | 74.6 | 18.1 | |
| 3,2 | Ac | ? | 23.4
23.8 | |
| 3 | aDGalpN | 99.8 | 51.1 | 68.2 | 79.4 | 72.6 | 62.6 | |
| 2 | Ac | ? | 23.4
23.8 | |
| | aDGlcpN | 95.6 | 53.0 | 79.2 | 72.0 | 71.8 | 62.6 | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":176.1,"l":"1","c":[0,0,225]},{"s":72.8,"l":"2","c":[0,0,225]},{"s":79.7,"l":"3","c":[0,0,225]},{"s":46.2,"l":"4","c":[0,0,225]},{"s":180.8,"l":"5","c":[0,0,225]},{"s":19.5,"l":"6","c":[0,0,225]},{"s":23.5,"l":"7","c":[0,0,225]},{"s":105.7,"l":"1","c":[230,0,30]},{"s":72.7,"l":"2","c":[230,0,30]},{"s":57.4,"l":"3","c":[230,0,30]},{"s":74.4,"l":"4","c":[230,0,30]},{"s":74.6,"l":"5","c":[230,0,30]},{"s":18.1,"l":"6","c":[230,0,30]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":99.8,"l":"1","c":[0,165,0]},{"s":51.1,"l":"2","c":[0,165,0]},{"s":68.2,"l":"3","c":[0,165,0]},{"s":79.4,"l":"4","c":[0,165,0]},{"s":72.6,"l":"5","c":[0,165,0]},{"s":62.6,"l":"6","c":[0,165,0]},{"s":23.6,"l":"2","c":[0,0,0]},{"s":95.6,"l":"1","c":[120,0,225]},{"s":53,"l":"2","c":[120,0,225]},{"s":79.2,"l":"3","c":[120,0,225]},{"s":72,"l":"4","c":[120,0,225]},{"s":71.8,"l":"5","c":[120,0,225]},{"s":62.6,"l":"6","c":[120,0,225]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Found 
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