title: Synthesis of a glycomimetic oligonucleotide conjugate by 1,3-dipolar cycloaddition.
abstract: A glycomimetic oligonucleotide conjugate bearing four galactose residues on a mannose core is -synthesized using oligonucleotide solid-phase synthesis and Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC, or "click" chemistry). To achieve this purpose, new building blocks (including the solid support and phosphoramidites) are synthesized and used on a DNA synthesizer to generate a tetraalkyne oligonucleotide, which is then conjugated with a galactose azide derivative by click chemistry to afford the desired 3'-tetragalactosyl-mannose oligonucleotide conjugate. The procedures described in this chapter provide a general approach for the synthesis of novel glycoconjugates that can be immobilized to a DNA chip via DNA-directed immobilization to study, for example, their multivalent interactions with lectins in cellular targeting/uptake, etc.
authors.forename: Gwladys
authors.initials: G
authors.lastname: Pourceau
authors.forename: Albert
authors.initials: A
authors.lastname: Meyer
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Vasseur
authors.forename: François
authors.initials: F
authors.lastname: Morvan
mesh_terms: D000478:Alkylation; D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D001483:Base Sequence; D040761:Biomimetic Materials / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry; D004980:Ethane / Q000737:chemistry; D005690:Galactose / Q000737:chemistry*; D006031:Glycosylation; D006868:Hydrolysis; D008358:Mannose / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry* / Q000235:genetics; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000480:Alkynes; D001386:Azides; D009841:Oligonucleotides; D003300:Copper; D004980:Ethane; D008358:Mannose; D005690:Galactose