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Keywords:

  • biphenyls;
  • DNA recognition;
  • hydrophobic bases;
  • oligonucleotides;
  • stacking interactions

Abstract

Thumbnail image of graphical abstract

Even saturated carbocycles are compatible with Watson–Crick pairing, as shown by the incorporation of phenylcyclohexyl-C-nucleoside pairs into the center of a DNA double helix (see picture). The increase in duplex stability arises from cyclohexyl/phenyl CH/π interactions. This makes the system an interesting scaffold for studying hydrophobic interactions and allows for the incorporation of additional molecular entities into the double helix.