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Synthesis 2014; 46(20): 2815-2825
DOI: 10.1055/s-0034-1378451
DOI: 10.1055/s-0034-1378451
paper
Synthesis of C4-Linked C0- and C2-Imidazole 2′-Deoxyribonucleoside Phosphoramidites and Imidazole Base-Pairing Effects on DNA
Further Information
Publication History
Received: 20 May 2014
Accepted after revision: 17 June 2014
Publication Date:
31 July 2014 (online)
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Abstract
The synthesis of C4-linked imidazole C0- and C2-2′-deoxyribonucleoside phosphoramidites (dPAs), in which the final phosphitylations are greatly improved by 4,5-dicyanoimidazole-promoted conversion, is described. The respective dPAs are successfully incorporated into the sequence of a 15-nt DNA, and the abilities of one or two imidazoles to pair with different bases are investigated through thermal melting (T m) experiments on the resulting DNA duplexes. Furthermore, computational models of the imidazole-modified DNAs are found to be in good agreement with the results of the thermal melting experiments.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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For oligodeoxyribonucleotides containing an imidazole N-nucleoside, see:
For recent reviews on C-nucelosides, see:
For the synthesis of C4-linked imidazole 2′-deoxyribo-nucleosides, see: