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Synthesis and properties of oligonucleotides that contain a triazole‐linked nucleic acid dimer
Author(s) -
Efthymiou Tim C.,
Desaulniers JeanPaul
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.532
Subject(s) - chemistry , oligonucleotide , dimer , phosphoramidite , nucleic acid , combinatorial chemistry , triazole , cycloaddition , oligonucleotide synthesis , monomer , 1,3 dipolar cycloaddition , nucleoside , click chemistry , rna , stereochemistry , dna , organic chemistry , biochemistry , catalysis , polymer , gene
New chemically modified oligonucleotides at the site of the backbone are needed to improve the properties of oligonucleotides. A practical synthesis for a triazole‐linked nucleoside dimer based on a PNA‐like structure has been developed. This involves synthesizing two uracil‐based monomers that contain either an azide or an alkyne functionality, followed by copper‐catalyzed 1,3‐dipolar cycloaddition . This dimer was incorporated within an oligonucleotide via phosphoramidite chemistry and UV‐monitored thermal denaturation data illustrates slight destabilization relative to its target complementary sequence. This chemically modified dimer will allow for a future investigation of its properties within DNA and RNA‐based applications. J. Heterocyclic Chem., (2011).