Base-Pairing Properties of Double-Headed Nucleotides

Mick Hornum, Julie Stendevad, Pawan K. Sharma, Pawan Kumar, Rasmus B. Nielsen, Michael Petersen, Poul Nielsen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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.

Original languageEnglish
JournalChemistry: A European Journal
Volume25
Issue number30
Pages (from-to)7387-7395
ISSN0947-6539
DOIs
Publication statusPublished - 28. May 2019

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Keywords

  • 2,6-diaminopurine
  • double-headed nucleotides
  • hypoxanthine
  • oligonucleotides

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