Probe design and synthesis of Galbeta(1-->3)[NeuAcalpha(2-->6)]GlcNAcbeta(1-->2)Man motif of N-glycan.
Synthesis and clusterization of Galbeta(1-->3)[NeuAcalpha(2-->6)]GlcNAcbeta(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, Galbeta(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 fluorescence- or radioactive reporter groups through either cross metathesis, acylation, Cu(I)-mediated Huisgen [2+3]-cycloaddition, or the azaelectrocyclization to utilize the various biological techniques.
Bao
Guang-ming
GM
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
Tanaka
Katsunori
K
Ikenaka
Kazuhiro
K
Fukase
Koichi
K
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D015335:Molecular Probes / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D015335:Molecular Probes; D011134:Polysaccharides