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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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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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.
AbstractList 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.
When nitric oxide was bubbled into acetonitrile under aerobic conditions, the solution showed a cobalt-blue color. Addition of guanosine into the solution generated N-2-acetylguanosine as a major product. The result of the reaction using N-15 labeled acetonitrile indicated that the nitrogen atom of the acetylated exocyclic amino group on N-2-acetylguanosine originated from acetonitrile. We discuss the reaction mechanism for the acylation.
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.「Results and Discussion」Nitric oxide (NO) is synthesized in various types of cells by the enzyme nitric oxide synthase and is involved in numerous biological functions including vasodilation, neurotransmission, and inflammation.2,3) Although NO is a radical, the reactivity of NO per se is relatively low.4) However, in the presence of O2, NO is converted to a reactive nitrosating reagent, dinitrogen trioxide (N2O3).5) N2O3 can react with amino groups in various biological molecules resulting in corresponding N-nitroso compounds. Amino groups of nucleic acid components react with N2O3 resulting in deamination compounds,6,7) since the formed N-nitroso compounds are unstable and subsequent hydrolyses are performed.
Author Fukai, Toshimitsu
Seki, Yusuke
Suzuki, Toshinori
Inukai, Michiyo
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Keywords acetylation
nitric oxide
NITROUS-ACID
GENOTOXICITY
guanosine
MECHANISM
DNA-DAMAGE
ELECTRONIC-SPECTRUM
acetonitrile
DINITROGEN TRIOXIDE
2'-DEOXYGUANOSINE
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Snippet When nitric oxide was bubbled into acetonitrile under aerobic conditions, the solution showed a cobalt-blue color. Addition of guanosine into the solution...
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StartPage 89
SubjectTerms 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
Title Acetylation of the Amino Group on Guanosine Induced by Nitric Oxide in Acetonitrile under Aerobic Conditions
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