New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves.
The synthesis of cyclic, branched, and bicyclic oligonucleotides was performed by copper-catalyzed azide-alkyne cycloaddition assisted by microwaves in solution and on solid support. For that purpose, new phosphoramidite building blocks and new solid supports were designed to introduce alkyne and bromo functions into the same oligonucleotide by solid-phase synthesis on a DNA synthesizer. The bromine atom was then substituted by sodium azide to yield azide oligonucleotides. Cyclizations were found to be more efficient in solution than on solid support. This method allowed the efficient preparation of cyclic (6- to 20-mers), branched (with one or two dangling sequences), and bicyclic (2 x 10-mers) oligonucleotides.
Lietard
Jory
J
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Université Montpellier 1, Université Montpellier 2, Place Eugène Bataillon, CC1704, 34095 Montpellier Cedex 5, France.
Meyer
Albert
A
Vasseur
Jean-Jacques
JJ
Morvan
François
F
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D008872:Microwaves; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D013237:Stereoisomerism
D009841:Oligonucleotides; D003300:Copper