Anomeric and Enantiomeric 2'-Deoxycytidines: Base Pair Stability in the Absence and Presence of Silver Ions

Chemistry. 2021 Jul 21;27(41):10574-10577. doi: 10.1002/chem.202101253. Epub 2021 Jun 10.

Abstract

Dodecamer duplex DNA containing anomeric (α/β-d) and enantiomeric (β-l/β-d) 2'-deoxycytidine mismatches was studied with respect to base pair stability in the absence and presence of silver ions. Stable duplexes with silver-mediated cytosine-cytosine pairs were formed by all anomeric and enantiomeric combinations. Stability changes were observed depending on the composition of the mismatches. Most strikingly, the new silver-mediated base pair of anomeric α-d-dC with enantiomeric β-l-dC is superior to the well-noted β-d/β-d-dC pair in terms of stability. CD spectra were used to follow global helical changes of DNA structure.

Keywords: DNA duplexes; anomers; deoxycytidine; enantiomers; oligonucleotides; silver.

MeSH terms

  • Base Pair Mismatch
  • Base Pairing
  • Cytosine
  • DNA*
  • Ions
  • Nucleic Acid Conformation
  • Silver*

Substances

  • Ions
  • Silver
  • Cytosine
  • DNA