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• W2049792079 endingPage "16" @default.
• W2049792079 startingPage "5" @default.
• W2049792079 abstract "Development of universal hybridization probes, that is, oligonucleotides displaying identical affinity toward matched and mismatched DNA/RNA targets, has been a longstanding goal due to potential applications as degenerate PCR primers and microarray probes. The classic approach toward this end has been the use of “universal bases” that either are based on hydrogen-bonding purine derivatives or aromatic base analogues without hydrogen-bonding capabilities. However, development of probes that result in truly universal hybridization without compromising duplex thermostability has proven challenging. Here we have used the “click reaction” to synthesize four C2′-pyrene-functionalized triazole-linked 2′-deoxyuridine phosphoramidites. We demonstrate that oligodeoxyribonucleotides modified with the corresponding monomers display (a) minimally decreased thermal affinity toward DNA/RNA complements relative to reference strands, (b) highly robust universal hybridization characteristics (average differences in thermal denaturation temperatures of matched vs mismatched duplexes involving monomer W are <1.7 °C), and (c) exceptional affinity toward DNA targets containing abasic sites opposite of the modification site (ΔTm up to +25 °C). The latter observation, along with results from absorption and fluorescence spectroscopy, suggests that the pyrene moiety is intercalating into the duplex whereby the opposing nucleotide is pushed into an extrahelical position. These properties render C2′-pyrene-functionalized triazole-linked DNA as promising universal hybridization probes for applications in nucleic acid chemistry and biotechnology." @default.
• W2049792079 created "2016-06-24" @default.
• W2049792079 creator A5024908822 @default.
• W2049792079 creator A5083305793 @default.
• W2049792079 date "2011-11-16" @default.
• W2049792079 modified "2023-09-26" @default.
• W2049792079 title "C2′-Pyrene-Functionalized Triazole-Linked DNA: Universal DNA/RNA Hybridization Probes" @default.
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• W2049792079 doi "https://doi.org/10.1021/jo201845z" @default.
• W2049792079 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3253902" @default.
• W2049792079 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22087648" @default.
• W2049792079 hasPublicationYear "2011" @default.
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