Acetylation of the Amino Group on Guanosine Induced by Nitric Oxide in Acetonitrile under Aerobic Conditions

Abstract

When nitric oxide was bubbled into acetonitrile under aerobic conditions, the solution showed a cobalt-blue color. Addition of guanosine into the solution generated N²-acetylguanosine as a major product. The result of the reaction using ¹⁵N labeled acetonitrile indicated that the nitrogen atom of the acetylated exocyclic amino group on N²-acetylguanosine originated from acetonitrile. We discuss the reaction mechanism for the acylation.