Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 30, Pages 7387-7395Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201901077
Keywords
2,6-diaminopurine; double-headed nucleotides; hypoxanthine; oligonucleotides
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Funding
- Danish National Research Foundation
- Danish Council for Independent Research \ Natural Sciences (FNU)
- Danish e-Infrastructure Cooperation (DeIC) National HPC Centre, SDU
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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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