Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: nosocomial infections [ICD11:
XB25 
]
The structure was elucidated in this paperNCBI PubMed ID: 24785390Publication DOI: 10.1016/j.carres.2014.03.004Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: P. Kosma <paul.kosma
boku.ac.at>
Institutions: Department of Chemistry, University of Natural Resources and Life Sciences, Muthgasse 18, A-1190 Vienna, Austria, Research Center Borstel, Parkallee 22, D-23845, Germany
The α-D-glucopyranosyl-(1→5)-substituted methyl glycosides of 3-deoxy-α-D-manno-oct-2-ulosonic acid (Kdo), 3-deoxy-α-D-lyxo-hept-2-ulosonic acid (Kdh), and d-glycero-α-D-talo-oct-2-ulosonic acid (Ko) were prepared using orthogonally protected glycosyl acceptor derivatives via glycosylation with a torsionally disarmed 4,6-O-benzylidene protected trifluoroacetimidate glucosyl donor followed by global deprotection. The related 6-O-phosphoryl-α-D-glucopyranosyl-(1→5)-substituted Kdo and Kdh derivatives were derived from a benzylidene-protected glucosyl intermediate using phosphoramidite and phosphoryl chloride-based phosphorylation steps, respectively. The deprotected disaccharides serve as ligands to study lectin binding of Acinetobacter lipopolysaccharide core oligosaccharides.
Lipopolysaccharide, Acinetobacter, Kdo, oligosaccharide synthesis, Ko
Structure type: oligomer ; 413.1296
C
15H
25O
13-
Location inside paper: p.68, scheme 2, 13
Trivial name: α-D-glucopyranosyl-(1-5)-sodium (methyl 3-deoxy-α-D-manno-2-oct-2-ulopyranosid)onate
Contained glycoepitopes: IEDB_130650,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, NMR, TLC, ESI-MS, chemical synthesis, chemical methods, glycosylation, RP-HPLC, ESI-TOF-MS
Synthetic data: chemical
Comments, role: synthetical product. NMR data are for Na+ salt.
Related record ID(s): 30121, 30440, 30441, 30442, 30443
NCBI Taxonomy refs (TaxIDs): 29430
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
1,5 aDGlcp 100.71 72.80 73.70 70.05 72.51 60.77
1 aXKdop 176.03 101.29 35.47 66.60 75.95 72.35 69.24 63.94
Me 51.42
1H NMR data: present in publication
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 1,5 | aDGlcp | 100.71 | 72.80 | 73.70 | 70.05 | 72.51 | 60.77 | |
| 1 | aXKdop | 176.03 | 101.29 | 35.47 | 66.60 | 75.95 | 72.35 | 69.24 | 63.94 |
| | Me | 51.42 | |
|
There is only one chemically distinct structure:
Found 
report error