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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
1,5	aDGlcp	100.98	72.49	73.88	69.86	72.82	60.77
1	aXKop	174.16	103.26	72.76	66.95	77.19	71.75	68.96	63.87
	Me	51.64

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@@]1(C(=O)O)O[C@H]([C@H](O)CO)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]1O

430.359 g/mol (C₁₅H₂₆O₁₄)