title: Synthesis of fluorescence-labeled Galbeta1-3Fuc and Galbeta1-4Fuc as probes for the endogenous glyco-epitope recognized by galectins in Caenorhabditis elegans.
abstract: To search for the endogenous glyco-epitope in Caenorhabditis elegans, we synthesized labeled Galbeta1-3Fuc and Galbeta1-4Fuc and examined their binding affinity for C. elegans galectin LEC-6 using frontal affinity chromatography analysis. We developed a new strategy for synthesizing the labeled saccharides, in which the labeling unit, the 2-aminopyridine moiety, is coupled with a spacer unit derived from D-mannitol. Our results indicate that Galbeta1-4Fuc is the endogenous glyco-epitope present in C. elegans N-glycans.
authors.affiliation: School of Pharmaceutical Sciences, Teikyo University, Sagamihara, Kanagawa, Japan.
authors.forename: Kazusa
authors.initials: K
authors.lastname: Nishiyama
authors.forename: Atsushi
authors.initials: A
authors.lastname: Yamada
authors.forename: Miki
authors.initials: M
authors.lastname: Takahashi
authors.forename: Tomoharu
authors.initials: T
authors.lastname: Takeuchi
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Kasai
authors.forename: Susumu
authors.initials: S
authors.lastname: Kobayashi
authors.forename: Hideaki
authors.initials: H
authors.lastname: Natsugari
authors.forename: Hideyo
authors.initials: H
authors.lastname: Takahashi
mesh_terms: D000631:Aminopyridines / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D001665:Binding Sites; D017173:Caenorhabditis elegans / Q000737:chemistry*; D002846:Chromatography, Affinity / Q000379:methods*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D037161:Galectins / Q000302:isolation & purification*; D008353:Mannitol / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000631:Aminopyridines; D004187:Disaccharides; D005456:Fluorescent Dyes; D037161:Galectins; C550965:galactopyranosyl-1-3-fucose; C547518:galactopyranosyl-1-4-fucose; D008353:Mannitol; C032439:alpha-aminopyridine