2023
DOI: 10.3390/sym15020342
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On Analogies in Proton-Transfers for Pyrimidine Bases in the Gas Phase (Apolar Environment)—Cytosine Versus Isocytosine

Abstract: Inter- and intra-molecular proton-transfers between functional groups in nucleobases play a principal role in their interactions (pairing) in nucleic acids. Although prototropic rearrangements (intramolecular proton-transfers) for neutral pyrimidine bases are well documented, they have not always been considered for their protonated and deprotonated forms. The complete isomeric mixtures in acid-base equilibria and in acidity–basicity parameters have not yet been examined. Taking into account the lack of litera… Show more

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Cited by 3 publications
(3 citation statements)
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“…[18,22,28,49,[57][58][59][60][61][62][63][64][65]. The DFT results for protonated and deprotonated tautomersrotamers of cytosine and isocytosine have just been reported for the complete tautomeric mixtures [66].…”
Section: Quantum-chemical Methods Applied To Tautomeric Nucleobases I...mentioning
confidence: 99%
“…[18,22,28,49,[57][58][59][60][61][62][63][64][65]. The DFT results for protonated and deprotonated tautomersrotamers of cytosine and isocytosine have just been reported for the complete tautomeric mixtures [66].…”
Section: Quantum-chemical Methods Applied To Tautomeric Nucleobases I...mentioning
confidence: 99%
“…Isocytosine exists in two oxo tautomers which are available in aqueous solution (18)(19)(20)(21). However, Vranken (22) has reported for some other tautomers which are formed when matrix isolated isocytosine is irradiated with UV light (λmax=308 nm) about 45 min.…”
Section: Introductionmentioning
confidence: 99%
“…Prototropism is essential for many biological and biochemical processes [8]. For example, it is a critical factor in modifying the properties of neutral or Molecules 2023, 28, 5684 2 of 19 protonated bases in nucleic acids, leading to mispairing and, subsequently, mutations [9,10]. Also, tautomerism is responsible for various simple carbohydrate forms in biosystems [11].…”
Section: Introductionmentioning
confidence: 99%