Highly stereoselective construction of 1,2-cis-D-quinovosamine glycosides for the synthesis of Pseudomonas aeruginosa O-antigen disaccharide

The highly stereoselective synthesis of complex carbohydrates containing 1,2-cis-quinovosamine is an on-going challenge. Here, we report a synergistic strategy of merging reagent modulation and acyl remote participation for highly stereoselective construction of 1,2-cis-D-quinovosamine linkages. The strategy is applied to the preparation of natural disaccharide present on the surface of Pseudomonas aeruginosa bacteria. The resulting disaccharide can be covalently bound to microarray surface or carrier via the aminopentyl linker at the reducing end, allowing for exploring its antigenic and immunogenic properties.