October

Picture of the Month - October 2021

Reactivity of alkylating Agents

Aziridinium ions are highly reactive electrophiles. They can be applied in organic synthesis as well as for the functionalization of molecules and surfaces. Furthermore, they are the intermediates of the alkylation of DNA by nitrogen mustards within a chemotherapy.

We are interested in tuning the reactivity of these electrophiles and for this purpose are studying bicyclic aziridinium ions, which we used to cross-link RNA and analyze its higher order structure. (doi.org/10.1093/nar/gkab468) Recently we were able to isolate the intermediate bicyclic aziridinium ions, obtain crystal structures and perform kinetic studies with these reactive species. (doi.org/10.1002/ejoc.202101072)

In the center of the picture, the crystal structure of a bicyclic aziridinium ion is shown together with its generation from a 3-chlorpiperidine and its reaction with a nucleobase. The background shows multiple stacked NMR spectra of a kinetic analysis and a DNA-fragment.

This picture was submitted by Prof. Dr. Richard Göttlich.

Further insights into the research activities of the ZfM groups can be found in the Gallery.