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 t he alpha-position are prone to an unusually facile hydrolytic deaminat ion. By conducting hydrolysis reactions in [O-18]water and analyzing t he reaction products by electrospray mass spectrometry, we find that d eamination occurs by direct attack of water at the beta-position of th e adenine ring system with displacement of the exocyclic amino group.