ArticleJournal of the American Society for Mass Spectrometry2002
The acidity of uracil and uracil analogs in the gas phase: four surprisingly acidic sites and biological implications.
Article in Journal of the American Society for Mass Spectrometry, 2002. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed, 83 citations in OpenAlex.
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- The effect of substrate and product transfer between polydisperse microdroplets on biological high-throughput screens.Scientific reports · 2026Article
- Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method.ACS omega · 2023Article
- Novel Aza-Paternò-Büchi Reaction Allows Pinpointing Carbon-Carbon Double Bonds in Unsaturated Lipids by Higher Collisional Dissociation.Analytical chemistry · 2022Article
- Experimental and Computational Studies on the Gas-Phase Acidity of 5,5-Dialkyl Barbituric Acids.Journal of the American Society for Mass Spectrometry · 2021Article
- Kinetic hydricity of silane hydrides in the gas phase.Chemical science · 2019Article
- Ground State Destabilization in Uracil DNA Glycosylase: Let's Not Forget "Tautomeric Strain" in Substrates.Journal of the American Chemical Society · 2019Article
- Experimental and Computational Gas Phase Acidities of Conjugate Acids of Triazolylidene Carbenes: Rationalizing Subtle Electronic Effects.Journal of the American Chemical Society · 2017Article
- Microhydration of Deprotonated Nucleobases.Journal of the American Society for Mass Spectrometry · 2016Article
- Crystal structures of 4-phenyl-piperazin-1-ium 6-chloro-5-ethyl-2,4-dioxopyrimidin-1-ide and 4-phenyl-piperazin-1-ium 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide.Acta crystallographica. Section E, Crystallographic communications · 2015Article
- On the mechanism of RNA phosphodiester backbone cleavage in the absence of solvent.Nucleic acids research · 2015Article
- Mass spectrometry and theoretical studies on N-C bond cleavages in the N-sulfonylamidino thymine derivatives.Journal of the American Society for Mass Spectrometry · 2015Article
- 4-(2-Meth-oxy-phen-yl)piperazin-1-ium 6-chloro-5-isopropyl-2,4-dioxopyrimidin-1-ide.Acta crystallographica. Section E, Structure reports online · 2014Article
- Dehydrogenative alkenylation of uracils via palladium-catalyzed regioselective C-H activation.Chemical communications (Cambridge, England) · 2013Article
- Gas-phase studies of substrates for the DNA mismatch repair enzyme MutY.Journal of the American Chemical Society · 2012Article
- Specificity of human thymine DNA glycosylase depends on N-glycosidic bond stability.Journal of the American Chemical Society · 2006Article
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2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The gas phase acidities of a series of uracil derivatives (1-methyluracil, 3-methyluracil, 6-methyluracil, 5,6-dimethyluracil, and 1,3-dimethyluracil) have been bracketed to provide an understanding of the intrinsic reactivity of uracil. The experiments indicate that in the gas phase, uracil has four sites more acidic than water. Among the uracil analogs, the N1-H sites have deltaH(acid) values of 331-333 kcal mol(-1); the acidity of the N3 sites fall between 347-352 kcal mol(-1). The vinylic C6 in 1-methyluracil and 3-methyluracil brackets to 363 kcal mol(-1), and 369 kcal mol(-1) in 1,3-dimethyluracil; the C5 of 1,3-dimethyluracil brackets to 384 kcal mol(-1). Calculations conducted at B3LYP/6-31+G* are in agreement with the experimental values. The bracketing of several of these sites involved utilization of an FTMS protocol to measure the less acidic site in a molecule that has more than one acidic site, establishing the generality of this method. In molecules with multiple acidic sites, only the two most acidic sites were bracketable, which is attributable to a kinetic effect. The measured acidities are in direct contrast to in solution, where the two most acidic sites of uracil (N1 and N3) are indifferentiable. The vinylic C6 site is also particularly acidic, compared to acrolein and pyridine. The biological implications of these results, particularly with respect to enzymes for which uracil is a substrate, are discussed.
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