A new type of acyclic, achiral nucleoside analogue. How does it simulate nucleosides?
The new monomer 1 seems to be an excellent mimic of nucleosides with different sugar conformations (north, south, and envelope), because of the relatively free rotation around gamma, delta, and chi. The rotation around chi is primarily controlled by the repulsion between H6 and the two hydrogen atoms on C4' and not pi conjugation between the double bond and the nucleobase. A viable synthesis of the guanine monomer 8 is described.
Petersen
Asger B
AB
Department of Chemistry, University of Copenhagen, The H.C. Orsted Institute, Copenhagen, Denmark.
Boesen
Thomas
T
Dahl
Otto
O
D006147:Guanine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D012399:Rotation
D009705:Nucleosides; D006147:Guanine