Abstract

One of the major mechanisms of epigenetic control is methylation and demethylation of lysine residues in histone proteins. The desire to understand the function of these modifications promoted the development of artificial molecules that recognize and bind methyllysine. One focus of this presentation is on synthetic macrocycles and their ability to recognize differently methylated lysines. Recent developments and our own efforts in this area will be discussed. (Hanauer et al., Org. Biomol. Chem. 2017, 15, 1100; Gruber, ChemBioChem 2018, DOI: 10.1002/cbic.201800398.)
In the second part of the lecture the latest research on new synthetic routes for bridged caprolactams is presented. We recently established a facile synthetic pathway towards the 7,8-dioxo-6-aza­bicyclo­[3.2.1]­octane scaffold using readily available caprolactam esters. The latter are cyclized after adequate N-protection using strong, non-nucleophilic bases. Mechanistic details of this particular type of Dieckmann cyclization as well as side products and artefacts occurring during the reaction will be presented. (C. Weck et al., New J. Chem. 2017, 41, 9984.)