New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves.
Identifieur interne : 000178 ( France/Analysis ); précédent : 000177; suivant : 000179New strategies for cyclization and bicyclization of oligonucleotides by click chemistry assisted by microwaves.
Auteurs : Jory Lietard [France] ; Albert Meyer ; Jean-Jacques Vasseur ; François MorvanSource :
- The Journal of organic chemistry [ 0022-3263 ] ; 2008.
Descripteurs français
- KwdFr :
- MESH :
- effets des radiations : Oligonucléotides.
- synthèse chimique : Oligonucléotides.
- Catalyse, Chromatographie en phase liquide à haute performance, Cuivre, Cyclisation, Micro-ondes, Oligonucléotides, Structure moléculaire, Stéréoisomérie.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Oligonucleotides.
- chemical , chemistry : Copper, Oligonucleotides.
- chemical , radiation effects : Oligonucleotides.
- Catalysis, Chromatography, High Pressure Liquid, Cyclization, Microwaves, Molecular Structure, Stereoisomerism.
Abstract
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.
DOI: 10.1021/jo702177c
PubMed: 18067317
Affiliations:
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pubmed:18067317Le document en format XML
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<front><div type="abstract" xml:lang="en">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.</div>
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