Non-Nucleoside Building Blocks for Copper-Assisted and Copper-Free Click Chemistry for the Efficient Synthesis of RNA Conjugates
| Autor: | K. N. Jayaprakash, Muthiah Manoharan, Kallanthottathil G. Rajeev, Martin Maier, Jos P. Varghese, David Butler, Chang Geng Peng |
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| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure Oligonucleotide Organic Chemistry Alkyne RNA Nucleosides Oligonucleotide synthesis Biochemistry Combinatorial chemistry Cycloaddition chemistry.chemical_compound Monomer chemistry Organic chemistry Physical and Theoretical Chemistry Copper-free click chemistry Nucleoside Copper |
| Zdroj: | Organic Letters. 12:5410-5413 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol102205j |
| Popis: | Novel non-nucleoside alkyne monomers compatible with oligonucleotide synthesis were designed, synthesized, and efficiently incorporated into RNA and RNA analogues during solid-phase synthesis. These modifications allowed site-specific conjugation of ligands to the RNA oligonucleotides through copper-assisted (CuAAC) and copper-free strain-promoted azide-alkyne cycloaddition (SPAAC) reactions. The SPAAC click reactions of cyclooctyne-oligonucleotides with various classes of azido-functionalized ligands in solution phase and on solid phase were efficient and quantitative and occurred under mild reaction conditions. The SPAAC reaction provides a method for the synthesis of oligonucleotide-ligand conjugates uncontaminated with copper ions. |
| Databáze: | OpenAIRE |
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