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Updated: May 10, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Deconvoluting the reactivity of two intermediates formed from modified pyrimidines
Liwei Weng1, Sonia M Horvat, Carl H Schiesser
1Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore Maryland 21218, USA.
Abstract:
Generation of the 5-(2'-deoxyuridinyl)methyl radical (6) was reexamined. Trapping by 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl confirms that 6 is generated. However, trapping by methoxyamine reveals that the respective carbocation (10) is also produced. Examining the effects of these traps on products in DNA reveals that the carbocation and not 6 yields interstrand cross-links. Cross-link formation from the carbocation is consistent with DFT calculations that predict that addition at the N1 position of dA is essentially barrierless.
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