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• W1994384654 abstract "We report the isolation and characterization for the first time of a cross‐link lesion between two adjacent cytosines from the 2‐methyl‐1,4‐naphthoquinone (menadione)‐sensitized 365‐nm irradiation of d(CpC). Electrospray ionization mass spectrometry (ESI‐MS), tandem MS and 1 H NMR results indicate that the cross‐link occurs between the C5 carbon atom of one cytosine and the N4 nitrogen atom of the other cytosine. Furthermore, we synthesized d(CpC) with a 15 N being incorporated on the amino group of either of the two cytosines. We then irradiated the two 15 N‐labeled dinucleoside monophosphates, isolated the cross‐link products and characterized them by MS and multi‐stage tandem MS. The latter results established unambiguously that the N4 nitrogen atom of the 3′‐nucleobase is involved in the covalent bond formation between the two cytosines. This, in combination with two‐dimensional nuclear Overhauser effect spectroscopy (NOESY) results, demonstrates that the cross‐link arises from the formation of a covalent bond between the C5 carbon atom of the 5′ cytosine and the N4 nitrogen atom of the 3′ cytosine. We also show that the solution pH has a significant effect on the formation of the cross‐link lesion, which supports that the deprotonation at the exocyclic amino group of cytosine cation radical is essential for the formation of the cross‐link lesion." @default.
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• W1994384654 date "2003-09-15" @default.
• W1994384654 modified "2023-10-17" @default.
• W1994384654 title "Identification and characterization of a novel cross-link lesion in d(CpC) upon 365-nm irradiation in the presence of 2-methyl-1,4-naphthoquinone" @default.
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• W1994384654 doi "https://doi.org/10.1093/nar/gkg736" @default.
• W1994384654 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/203320" @default.
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