Synthesis of N-(N-bromoacetylglycyl)-β-D-glycopyranosylamines, derivatives of monoand di-α-L-fucosylated diand trisaccharides

Abstract

N-(N-Bromoacetylglycyl)-β-glycopyranosylamines of diand trisaccharides, namely, α-LFucp-(1→6)-β-D-GlcNAcp-NHCOCH₂NHCOCH₂Br, α-L-Fucp-(1→3)-β-D-GlcNAcpNHCOCH₂NHCOCH₂Br, α-L-Fucp-(1→6)-[α-L-Fucp-(1→3)]-β-D-GlcNAcp-NHCOCH₂NHCOCH₂Br, α-L-Fucp-(1→4)-[β-D-Galp-(1→3)]-β-D-GlcNAcp-NHCOCH₂NHCOCH₂Br, and α-L-Fucp-(1→2)-β-D-Galp-(1→4)-β-D-Glcp-NHCOCH₂NHCOCH2Br, were synthesized in ~70% yields by treatment of the appropriate N-glycyl-β-glycopyranosylamines with N-bromoacetoxysuccinimide in aqueous DMF. The synthesized diand trisaccharide bromo derivatives are proposed for the obtaining of neoglycoconjugates of physiologically active substances, for instance, of daunorubicin anticancer agent.