The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Formation of 13C-, 15N-, and 18O-Labeled Guanidinohydantoin from Guanosine Oxidation with Singlet Oxygen. Implications for Structure and Mechanism
Abstract
Guanosine labeled with 15N at N1, amino, and N7 and 13C at either C2 or C8 was oxidized by Rose Bengal photosensitization (singlet oxygen) in buffered aqueous solution. At pH > 7, spiroiminodihydantoin was the major product, while at pH < 7, guanidinohydantoin (Gh) was the principal product. 15N and 13C NMR studies confirmed that Gh was formed as a mixture of slowly equilibrating diastereomers. Experiments conducted in H218O indicated that Gh and Sp each contained one oxygen atom derived from O2 and one from H2O. Tandem mass spectrometry was used to identify the C4 carbonyl of Gh as the one labeled with 18O, supporting a mechanism involving attack of water at C5 of a dehydro-8-oxoguanosine intermediate.
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Cites
Oxidative Nucleobase Modifications Leading to Strand Scission
Burrows, C. J., & Muller, J. G. (1998) · Chemical Reviews · doi:10.1021/cr960421s · Cited by 1,736
Self-citationMutagenicity and repair of oxidative DNA damage: insights from studies using defined lesions
Wang, D., Kreutzer, D. A., & Essigmann, J. M. (1998) · Mutation research. Fundamental and molecular mechanisms of mutagenesis · doi:10.1016/s0027-5107(98)00066-9 · Cited by 464
Sheu, C., Kang, P., Khan, S., & Foote, C. S. (2002) · Journal of the American Chemical Society · doi:10.1021/ja011696e · Cited by 78
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Singlet Molecular Oxygen Reactions with Nucleic Acids, Lipids, and Proteins
Di Mascio, P., Martinez, G. R., Miyamoto, S., Ronsein, G. E., Medeiros, M. H. G., & Cadet, J. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00554 · Cited by 659
Cadet, J., Douki, T., & Ravanat, J.-L. (2008) · Accounts of Chemical Research · doi:10.1021/ar700245e · Cited by 555
Formation of UV-induced DNA damage contributing to skin cancer development
Cadet, J., & Douki, T. (2018) · Photochemical & Photobiological Sciences · doi:10.1039/c7pp00395a · Cited by 435
Singlet Oxygen Oxidation of Isolated and Cellular DNA: Product Formation and Mechanistic Insights
Cadet, J., Ravanat, J., Martinez, G. R., Medeiros, M. H. G., & Mascio, P. D. (2006) · Photochemistry and Photobiology · doi:10.1562/2006-06-09-ir-914 · Cited by 176
Telomeric DNA damage landscapes distinguish oxidative from inflammatory cellular stress
Fleming, A. M., & Burrows, C. J. (2025) · Nucleic Acids Research · doi:10.1093/nar/gkaf1320 · Cited by 6
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Metadata
- Authors
- Ye, Y., Muller, J. G., Luo, W., Mayne, C. L., Shallop, A. J., Jones, R. A., & Burrows, C. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-10-28
- Volume
- 125
- Issue
- 46
- Pages
- 13926-13927
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1976706105
- Cited by
- 167
- References
- 3
- FWCI
- 5.87
- Type
- journal article
- Language
- en
- Open access
- closed
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