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1. (Article ID: 4717)
Pokorny B, Müller-Loennies S, Kosma P
Synthesis of a-D-glucosyl substituted methyl glycosides of 3-deoxy-a-D-manno- and D-glycero-a-D-talo-oct-2-ulosonic acid (Kdo/Ko) corresponding to inner core fragments of Acinetobacter lipopolysaccharide
Carbohydrate Research 391 (2014)
66-81
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
NCBI PubMed ID: 24785390Publication DOI: 10.1016/j.carres.2014.03.004Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: P. 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
Methods: 13C NMR, NMR, TLC, ESI-MS, chemical synthesis, chemical methods, glycosylation, RP-HPLC, ESI-TOF-MS
The publication contains the following compound(s):
- Compound ID: 11767
|
a-Kdop-(2-4)-+
|
P-6)-+ | P-4)-+
| | |
a-D-3dlyxHepp-ulosaric-(2-6)-b-D-Glcp-(1-4)-a-D-3dlyxHepp-ulosaric-(2-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-/Variants 0/-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
/Variants 0/ is:
a-Kop-(2-6)-
OR (exclusively)
a-Kdop-(2-6)- |
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Structure type: oligomer
Compound class: core oligosaccharide
- Compound ID: 11768
Structure type: oligomer
; 413.1296
C15H25O13-
Trivial name: α-D-glucopyranosyl-(1-5)-sodium (methyl 3-deoxy-α-D-manno-2-oct-2-ulopyranosid)onate
- Compound ID: 11769
Structure type: oligomer
; 383.1193
C14H23O12-
Trivial name: α-D-glucopyranosyl-(1-5)-sodium (methyl 3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate
- Compound ID: 11770
Structure type: oligomer
; 493.0966
C15H26O16P-
Trivial name: 6-O-phosphono-α-D-glucopyranosyl-(1-5)-methyl 3-deoxy-α-D-manno-oct-2-ulopyranosidonic acid (sodium salt)
- Compound ID: 11771
Structure type: oligomer
; 463.0857
C14H24O15P-
Trivial name: 6-O-phosphono-α-D-glucopyranosyl-(1-5)-(methyl 3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onic acid (sodium salt)
- Compound ID: 11772
Structure type: oligomer
; 453.1210
C15H26O14Na+
Trivial name: α-D-glucopyranosyl-(1-5)-sodium (methyl D-glycero-α-D-talo-oct-2-ulopyranosid)onate
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