AN ASSESSMENT OF THE REACTIVITY OF GUANOSINE AND SOME OF ITS DERIVATIVES TO ELECTROPHILES BY (15)N-NMR SPECTROSCOPY.

Article abstract of DOI:10.1016/S0040-4020(01)87562-1

(15)N-NMR spectra of guanosine and uridine and several of their amide-protected derivatives have been studied.The nucleophilicity of the N⁷ of the guanosine, in some of its O⁶ and N¹ substituted derivatives, has been studied by folloving the (15)N chemical shift of the protonated species in the presence of CF3COOH.The formation of the N⁷ protonated species, the magnitude of its (15)N chemical shift and the potential of the N⁷ to undergo methylation reaction in a particular protected derivative of guanosine throws light on the efficiency of a protecting group to protect the guanine residue against an electrophile.