Investigation of hydrolytic deamination of 1-(-hydroxy-1-phenylethyl)adenosine

The ring nitrogen of adenosine reacts at both the alpha-(benzylic) and beta-carbons of styrene oxide to form 1-substituted products. The 1-(2-hydroxy-1-phenylethyl)adenosines formed by oxirane ring opening at the alpha-position are prone to an unusually facile hydrolytic deamination. By conducting hydrolysis reactions in [O-18]water and analyzing the reaction products by electrospray mass spectrometry, we find that deamination occurs by direct attack of water at the beta-position of the adenine ring system with displacement of the exocyclic amino group.