Synthesis of mannose and galactose oligonucleotide conjugates by bi-click chemistry.
Glyco oligonucleotide conjugates, each exhibiting two mannose and two galactose residues, were efficiently synthesized by two successive 1,3-dipolar cycloadditions (click chemistry). Two phosphoramidite derivatives were used: one bearing a bromoalkyl group as a precursor to azide functionalization and another bearing a propargyl group. After a first cycloaddition with a mannosyl-azide derivative, the bromine atoms were substituted with NaN(3) and a second click reaction was performed with a 1'-O-propargyl galactose, affording the heteroglyco oligonucleotide conjugate.
Pourceau
Gwladys
G
Institut des Biomolecules Max Mousseron, UMR 5247 CNRS, Universite Montpellier 1, Place Eugene Bataillon, CC1704, 34095 Montpellier Cedex 5, France.
Meyer
Albert
A
Vasseur
Jean-Jacques
JJ
Morvan
François
F
D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry; D008358:Mannose / Q000031:analogs & derivatives* / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D004247:DNA; D008358:Mannose; D005690:Galactose