5'-Bis-conjugation of oligonucleotides by amidative oxidation and click chemistry.
A pent-4-ynyl tert-butyl N,N-diisopropyl phosphoramidite was coupled at the 5'-end of oligonucleotides to give a phosphite triester linkage, which forms an H-phosphonate diester linkage during treatment with dichloroacetic acid. Then an amidative oxidation with CCl(4) in the presence of an amine and a 1,3-dipolar cycloaddition with an azide under copper(I) catalysis afforded the bis-conjugated oligonucleotides with high efficiency. The introduction of a bromoalkyl group as a precursor of azidoalkyl by amidative oxidation allowed the performance of two selective 1,3-dipolar cycloadditions.
Meyer
Albert
A
Institut des Biomolécules Max Mousseron, UMR 5247, CNRS Université Montpellier 1, Université Montpellier 2, CC1704, Place E. Bataillon, 34095 Montpellier Cedex 5, France.
Pourceau
Gwladys
G
Vasseur
Jean-Jacques
JJ
Morvan
François
F
D057930:Click Chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D004952:Esters; D009841:Oligonucleotides; D009943:Organophosphorus Compounds