Conformation of acetylaminofluorene and aminofluorene modified guanosine and guanosine derivatives

Abstract

Acetylaminofluorene and aminofluorene modified Guo, GMP, d(GpA) and d(ApG) have been studied by circular dichroism and 1H nuclear magnetic resonance. Aminofluorene modified Guo is preferentially in the anti conformation and acetylaminofluorene modified Guo in the syn conformation. It is proposed that the anti conformation of aminofluorene modified Guo is stabilized by an intra molecular hydrogen bond between the NH group of aminofluorene residue and the 5′-OH group of the sugar. The results on the modified dinucleoside monophosphates are analyzed according to this hypothesis.