3-Ureidoacrylonitriles: Novel products from the photoisomerization of cytosine, 5-methylcytosine, and related compounds

Journal Article · Wed Oct 10 04:00:00 EDT 1990 · Journal of the American Chemical Society; (USA)

DOI:https://doi.org/10.1021/ja00177a038· OSTI ID:6271629

Shaw, A A; Shetlar, M D ^[1]

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1. Univ. of California, San Francisco (USA)

During studies of the effects of far-ultraviolet light on DNA and its components, the authors have discovered that cytosine and 5-methylcytosine, as well as their nucleosides and N1-methyl derivatives, undergo photoisomerization reactions to yield the corresponding cis- and trans-3-ureidoacrylonitriles. For example, N1-methylcytosine reacts to give cis- and trans-3-(N3-methylureido)acrylonitrile. These products have been characterized through use of one- and two-dimensional high-resolution {sup 1}H and {sup 13}C NMR spectroscopy, ultraviolet and infrared spectroscopy, electron impact and liquid secondary ion mass spectrometry, and, in some cases, synthesis by an alternate route. Detailed {sup 13}C NMR data for the parent compounds are presented for comparison purposes. These photoisomerization reactions take place cleanly in acetonitrile; the corresponding reactions occur in aqueous solutions as well. For cytosine and 5-methylcytosine the photoreaction in acetonitrile is slow; however, the rate of reaction is greatly enhanced by N1 substitution.

• OSTI ID: 6271629
• Journal Information: Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 112:21; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

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560120* -- Radiation Effects on Biochemicals
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63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AMINES
AZINES
BIOLOGICAL EFFECTS
BIOLOGICAL RADIATION EFFECTS
CARBON 13
CARBON ISOTOPES
CYTOSINE
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NITRILES
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUCLEIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PYRIMIDINES
RADIATION EFFECTS
RADIATIONS
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