Synthesis of a spacer-armed disaccharide structurally related to the M antigenic fragment of Brucella O-polysaccharides

New synthesis of oligosaccharides modelling the M epitope of the Brucella O-polysaccharide

“…The filtrate was concentrated and the residue was subjected to gel-permeation chromatography to give title compound 4 (36 mg, 92%) as a white amorphous solid. The data of NMR and mass-spectra were identical to those described previously (Tsvetkov and Nifantiev, 2023). CON),103.5,103.4,103.1,102.9,101.9,79.4,79.2,79.0,78,7,78.6,78,4,77.5 70.1,70.0, 69.9, 69.6, 69.5, 69.2, 69.0, 68.9, 68.7, 68.6, 68.5, 68.3 78.8, 77.8, 77.5, 77.4 70.3, 70.0, 69.8, 69.7, 69.2, 69.1 69.0, 68.8, 68.7, 68.6, 68.2 3).…”

“…α-(1→2)-Linked oligomers of N-(3-deoxy-L-glycero-tetronoyl)-D-perosamine related to the O-polysaccharide of Vibrio cholerae O1 have been synthesized by the Kováć's group (Hou and Kovač, 2010;Mukherjee et al, 2019). Recently, we reported the synthesis of the (1→3)-linked disaccharide 4 (Figure 2) (Tsvetkov and Nifantiev, 2023), which corresponds to the unique structural element of the M epitope of the Brucella O-polysaccharide. Here, we report on the synthesis of larger oligosaccharides 1-3 that comprise the (1→3)linked disaccharide as a fragment.…”

DataSheet1.docx

“…The filtrate was concentrated and the residue was subjected to gel-permeation chromatography to give title compound 4 (36 mg, 92%) as a white amorphous solid. The data of NMR and mass-spectra were identical to those described previously (Tsvetkov and Nifantiev, 2023). CON),103.5,103.4,103.1,102.9,101.9,79.4,79.2,79.0,78,7,78.6,78,4,77.5 70.1,70.0, 69.9, 69.6, 69.5, 69.2, 69.0, 68.9, 68.7, 68.6, 68.5, 68.3 78.8, 77.8, 77.5, 77.4 70.3, 70.0, 69.8, 69.7, 69.2, 69.1 69.0, 68.8, 68.7, 68.6, 68.2 3).…”

“…α-(1→2)-Linked oligomers of N-(3-deoxy-L-glycero-tetronoyl)-D-perosamine related to the O-polysaccharide of Vibrio cholerae O1 have been synthesized by the Kováć's group (Hou and Kovač, 2010;Mukherjee et al, 2019). Recently, we reported the synthesis of the (1→3)-linked disaccharide 4 (Figure 2) (Tsvetkov and Nifantiev, 2023), which corresponds to the unique structural element of the M epitope of the Brucella O-polysaccharide. Here, we report on the synthesis of larger oligosaccharides 1-3 that comprise the (1→3)linked disaccharide as a fragment.…”