Acetylation of the amino group on guanosine induced by nitric oxide in acetonitrile under aerobic conditions.
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.
Suzuki
Toshinori
T
School of Pharmacy, Shujitsu University, Okayama, Japan. tsuzuki@shujitsu.ac.jp
Fukai
Toshimitsu
T
Seki
Yusuke
Y
Inukai
Michiyo
M
D000097:Acetonitriles / Q000737:chemistry*; D000107:Acetylation; D002851:Chromatography, High Pressure Liquid; D006151:Guanosine / Q000737:chemistry*; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D000097:Acetonitriles; D006151:Guanosine; D009569:Nitric Oxide; D010100:Oxygen; C032159:acetonitrile