387334-40-9Relevant academic research and scientific papers
The pH-Dependence of the Hydration of 5-Formylcytosine: an Experimental and Theoretical Study
Korotenko, Vasily,Zipse, Hendrik,Zott, Fabian L.
, (2022/02/17)
5-Formylcytosine is an important nucleobase in epigenetic regulation, whose hydrate form has been implicated in the formation of 5-carboxycytosine as well as oligonucleotide binding events. The hydrate content of 5-formylcytosine and its uracil derivative has now been quantified using a combination of NMR and mass spectroscopic measurements as well as theoretical studies. Small amounts of hydrate can be identified for the protonated form of 5-formylcytosine and for neutral 5-formyluracil. For neutral 5-formylcytosine, however, direct detection of the hydrate was not possible due to its very low abundance. This is in full agreement with theoretical estimates.
TET-Like Oxidation in 5-Methylcytosine and Derivatives: A Computational and Experimental Study
Jonasson, Niko S. W.,Jan?en, Rachel,Menke, Annika,Zott, Fabian L.,Zipse, Hendrik,Daumann, Lena J.
, p. 3333 - 3340 (2021/09/25)
The epigenetic marker 5-methylcytosine (5mC) is an important factor in DNA modification and epigenetics. It can be modified through a three-step oxidation performed by ten-eleven-translocation (TET) enzymes and we have previously reported that the iron(IV)-oxo complex [Fe(O)(Py5Me2H)]2+ (1) can oxidize 5mC. Here, we report the reactivity of this iron(IV)-oxo complex towards a wider scope of methylated cytosine and uracil derivatives relevant for synthetic DNA applications, such as 1-methylcytosine (1mC), 5-methyl-iso-cytosine (5miC) and thymine (T/5mU). The observed kinetic parameters are corroborated by calculation of the C?H bond energies at the reactive sites which was found to be an efficient tool for reaction rate prediction of 1 towards methylated DNA bases. We identified oxidation products of methylated cytosine derivatives using HPLC-MS and GC-MS. Thereby, we shed light on the impact of the methyl group position and resulting C?H bond dissociation energies on reactivity towards TET-like oxidation.
The (α-4) photoconjugates of 5-methylcytosine, 1,5-dimethylcytosine, 1-methylthymine and thymidine
Shetlar, Martin D.,Chung, Janet
experimental part, p. 336 - 343 (2012/08/08)
The pyrimidine nucleobases contained in DNA undergo a variety of photoinduced reactions in which two moieties become joined to form a product (e.g. formation of cyclobutane dimers and [6-4] adducts). Herein, we describe a new type of photoconjugation reaction that has been shown to occur for 5-methylcytosine (5-MeC), 1,5-dimethylcytosine (1,5-diMeC), 1-methylthymine and thymidine; in this reaction the 5-methyl group of one nucleobase (or nucleoside) becomes attached to the 4-position of the second moiety. For example, 5-MeC forms α-4′-(5′-methylpyrimidin-2′-one)-5-methylcytosine. The various (α-4) conjugates are produced upon irradiation of the parent compound in frozen aqueous solution at -78.5°C. The UV spectra of these compounds display a characteristic double humped profile, similar to that expected from overlaying the spectrum of parent nucleobase with that of a 2′-pyrimidone moiety. Preliminary results suggest that thymine and 5-methyl-2′-deoxycytidine (5-MedCyd) form analogous photoproducts. A variety of other previously unreported photoproducts are described as well for the 5-MeC, 1,5-diMeC and 5-MedCyd systems.
