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
1,5,6	P
1,5	aDGlcp	100.60	72.79	73.30	69.61	71.84	63.73
1	aD3dlyxHepp-ulosaric	175.95	100.99	35.16	66.31	76.46	73.95	61.63
	Me	51.31

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(=O)O)O1

478.296 g/mol (C₁₄H₂₃O₁₆P)