RESUMO
7-Deazaguanine (7-DeG) was developed as a hydrogen-bonding module capable of enhanced recognition of uracil (U) and thymine (T); a water-soluble derivative displayed high affinity and selectivity toward DNA and RNA duplexes containing single T- and U-bulges.
Assuntos
Guanina/análogos & derivados , Timina/química , Sequência de Bases , Guanina/química , Ligação de Hidrogênio , Ligantes , Uracila/químicaRESUMO
[structure: see text] UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligomerization of UG (K(assoc) approximately 230 M(-)(1), CDCl(3)). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (>10-fold higher K(assoc) for DeUG.DAN vs UG.DAN) but also dimerizes more strongly (K(dim) = 880 +/- 40 M(-)(1), CDCl(3)) by adopting a conformation preorganized for both binding and dimerization.
