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
1,5,6	P
1,5	aDGlcp	100.61	72.99	73.23	69.50	72.25	62.93
1	aXKdop	176.06	101.30	35.22	66.42	75.48	72.35	69.01	64.07
	Me	51.42

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CO[C@]1(C(=O)O)C[C@@H](O)[C@@H](O[C@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]([C@H](O)CO)O1

494.339 g/mol (C₁₅H₂₇O₁₆P)