Modified pyrimidine nucleobases and their chemical properties

Zott, Fabian Leonhard (2023): Modified pyrimidine nucleobases and their chemical properties: a theoretical and experimental study. Dissertation, LMU München: Fakultät für Chemie und Pharmazie

Abstract

The epigenetic marker 5-methylcytosine (5mC) is an important factor in DNA modification and epigenetic regulation. It can be modified through a sequential three-step oxidation performed by the ten-eleven-translocation (TET) enzymes, leading to 5-hydroxymethylcytosine (5hmC), 5-formylcytosine (5fC) and 5-caboxycytosine (5caC). This work investigates the pH-dependence of the hydration of 5-formylcytosine, alongside with its acid-base and bond dissociation properties. Additionally, we uncover the intrinsic de-/protonation states of 5caC and provide insights into the impact of the methyl group positions of pyrimidine nucleobases and resulting C−H bond dissociation energies in TET-like oxidation reactions with a biomimetic iron(IV)-oxo complex.

• Dokumententyp: Dissertationen (Dissertation, LMU München)
• Keywords: Epigenetics, Theoretical Chemistry, Pyrimidine Nucleobases, Bond Dissociation Energies, Acid and Base Properties
• Themengebiete: 500 Naturwissenschaften und Mathematik ; 500 Naturwissenschaften und Mathematik > 540 Chemie
• Fakultäten: Fakultät für Chemie und Pharmazie
• Sprache der Hochschulschrift: Englisch
• Datum der mündlichen Prüfung: 14. März 2023
• 1. Bericht­erstatter:in: Zipse, Hendrik