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: Faculty of Chemistry and Pharmacy

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.

• Item Type: Theses (Dissertation, LMU Munich)
• Keywords: Epigenetics, Theoretical Chemistry, Pyrimidine Nucleobases, Bond Dissociation Energies, Acid and Base Properties
• Subjects: 500 Natural sciences and mathematics; 500 Natural sciences and mathematics > 540 Chemistry and allied sciences
• Faculties: Faculty of Chemistry and Pharmacy
• Language: English
• Date of oral examination: 14. March 2023
• 1. Referee: Zipse, Hendrik
• Signature of the printed copy: 0001/UMC 30602