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 th...

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Bibliographic Details
Published inChemical & Pharmaceutical Bulletin Vol. 57; no. 1; pp. 89 - 91
Main Authors Suzuki, Toshinori, Fukai, Toshimitsu, Seki, Yusuke, Inukai, Michiyo
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 01.01.2009
Pharmaceutical Society of Japan
Pharmaceutical Soc Japan
Japan Science and Technology Agency
Subjects
acetonitrile
Acetonitriles - chemistry
Acetylation
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Chromatography, High Pressure Liquid
guanosine
Guanosine - chemistry
Life Sciences & Biomedicine
Molecular Structure
nitric oxide
Nitric Oxide - chemistry
Oxygen - chemistry
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
Spectrometry, Mass, Electrospray Ionization
acetylation
nitric oxide
NITROUS-ACID
GENOTOXICITY
guanosine
MECHANISM
DNA-DAMAGE
ELECTRONIC-SPECTRUM
acetonitrile
DINITROGEN TRIOXIDE
2'-DEOXYGUANOSINE
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.57.89