Base-Pairing Properties of Double-Headed Nucleotides |
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Authors: | Dr. Mick Hornum Julie Stendevad Dr. Pawan K. Sharma Dr. Pawan Kumar Rasmus B. Nielsen Dr. Michael Petersen Dr. Poul Nielsen |
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Affiliation: | 1. Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, 5230 Odense M, Denmark;2. Department of Chemistry, Kurukshetra University, Kurukshetra, Haryana, 136119 India |
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Abstract: | Nucleotides that contain two nucleobases (double-headed nucleotides) have the potential to condense the information of two separate nucleotides into one. This presupposes that both bases must successfully pair with a cognate strand. Here, double-headed nucleotides that feature cytosine, guanine, thymine, adenine, hypoxanthine, and diaminopurine linked to the C2′-position of an arabinose scaffold were developed and examined in full detail. These monomeric units were efficiently prepared by convergent synthesis and incorporated into DNA oligonucleotides by means of the automated phosphoramidite method. Their pairing efficiency was assessed by UV-based melting-temperature analysis in several contexts and extensive molecular dynamics studies. Altogether, the results show that these double-headed nucleotides have a well-defined structure and invariably behave as functional dinucleotide mimics in DNA duplexes. |
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Keywords: | 2,6-diaminopurine double-headed nucleotides hypoxanthine oligonucleotides |
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