Systematic synthesis of N-methyl-1-deoxynojirimycin-containing, Lex, Lea, sialyl-Lex and sialyl-Lea epitopes recognized by selectins

Add time:07/14/2019    Source:sciencedirect.com

A systematic synthesis of the N-methyl-1-deoxynojirimycin-containing oligosaccharides related to the Lewis x, Lewis a, sialyl-Lewis x and sialyl-Lewis a antigens has been achieved. The couplings of the suitably protected 1-deoxynojirimycin derivative 10 with methyl-1-thioglycosides (glycosyl donors) of l-fucose (11), d-galactose (15) and α-sialyl-(2→3)-d-galact (27) were carried out by using dimethyl (methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) as the glycosyl promoter. The resulting di- and tri-saccharides were each converted, by further cross glycosylations with 11, 15 or 27, to the desired tri- and tetra-saccharides 3–6 that inhibit the recognition between sialyl-Lewis x and selectins, a family of leukocyte cell adhesion molecules.

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