Oligonucleotide carbohydrate-centered galactosyl cluster conjugates synthesized by click and phosphoramidite chemistries.
Oligonucleotide glycoconjugates with a mannose or galactose core bearing four galactose residues introduced by phosphoramidite chemistry and copper catalyzed azide alkyne 1,3-dipolar cycloaddition (click chemistry) have been synthesized. A first click reaction allowed the introduction on a solid support of a mannose core on which four pentynyl linkers were introduced using a phosphoramidite derivative. After the elongation of the oligonucleotide, a second click reaction performed either on solid support or in solution allowed the introduction of four galactose azide derivatives. Repeating the phosphoramidite and click chemistries afforded an oligonucleotide glycoconjugate dendrimer bearing 16 galactoses on its periphery.
Pourceau
Gwladys
G
Institut des Biomolecules Max Mousseron, UMR 5247 CNRS, Universite Montpellier 1, Place Eugene Bataillon, Montpellier Cedex 5, France.
Meyer
Albert
A
Chevolot
Yann
Y
Souteyrand
Eliane
E
Vasseur
Jean-Jacques
JJ
Morvan
François
F
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D005690:Galactose / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001386:Azides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D003300:Copper; D008358:Mannose; D005690:Galactose