Stability and polymerase recognition of pyridine nucleobase analogues: role of minor-groove H-bond acceptors

Y. Kim, A.M. Leconte, Y. Hari, F.E. Romesberg, Angew. Chem. Int. Ed. (2006) 45:7809-7812.
Pyridyl nucleoside analogues are synthesized and characterized. An α-glycosidic nitrogen atom provides an H-bond acceptor that does not significantly facilitate pairing with natural nucleobases. However, it forms minor-groove H-bonds with water molecules and DNA polymerases that optimize the stability and replication, respectively, of the UBP.