Stable cyclohexyl-phenyl recognition in the center of a DNA duplex.
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/pi 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.
Kaufmann
Marco
M
Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland.
Gisler
Michael
M
Leumann
Christian J
CJ
D003510:Cyclohexanes / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013816:Thermodynamics; D044366:Transition Temperature
D003510:Cyclohexanes; D004247:DNA