Synthesis and molecular recognition of carbohydrate-centered multivalent glycoclusters by a plant lectin RCA120.
Water soluble and lectin-recognizable carbohydrate-centered glycoclusters were prepared efficiently by the Huisgen 1,3-cycloaddition reaction of methyl-2,3,4,6-tetra-O-propargyl beta-D-galactopyranoside with 2-azidoethyl glycosides of lactose and N-acetyllactosamine. Their binding by a plant lectin RCA120 was examined by capillary affinity electrophoresis using fluorescence-labeled asialoglycans from human alpha1-acid glycoprotein. The glycoclusters showed 400-fold stronger inhibitory effect than free lactose, manifesting strong multivalency effect.
Gao
Yongjun
Y
Department of Biology, Johns Hopkins University, 3400 North Charles Street, Baltimore, MD 21218, USA.
Eguchi
Atsuko
A
Kakehi
Kazuaki
K
Lee
Yuan C
YC
D001386:Azides / Q000138:chemical synthesis; D002240:Carbohydrate Sequence; D019075:Electrophoresis, Capillary; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D007785:Lactose / Q000138:chemical synthesis / Q000378:metabolism; D008969:Molecular Sequence Data; D009961:Orosomucoid / Q000737:chemistry*; D037121:Plant Lectins / Q000737:chemistry*; D011485:Protein Binding / Q000187:drug effects
D001386:Azides; D006001:Glycoconjugates; D006027:Glycosides; D009961:Orosomucoid; D037121:Plant Lectins; C017707:Ricinus communis agglutinin-1; D007785:Lactose