Probe design and synthesis of Galβ(1→3)[NeuAcα(2→6)]GlcNAcβ(1→2)Man motif of N-glycan
摘要:
Synthesis and clusterization of Gal beta(1 -> 3)[NeuAc alpha(2 -> 6)]GlcNAc beta(1 -> 2)Man motif of the N-glycan, as the molecular probes for their biological evaluation, are reported. Key step is the quantitative and the completely alpha-selective sialylation of the C5-azide N-phenyltrifluoroacetimidate with the disaccharide acceptor, Gal beta(1 -> 3) GlcNTroc. Clusterization of the 16 molecules of trisaccharide motif was also achieved by the 'self-activating click reaction'. These probes could efficiently be labeled by biotin and/or other fluorescenceor radioactive reporter groups through either cross metathesis, acylation, Cu(I)-mediated Huisgen [2+3]-cycloaddition, or the azaelectrocyclization to utilize the various biological techniques. (C) 2010 Elsevier Ltd. All rights reserved.