Site-Selective C-H Amination of Phenol-Containing Biomolecules

A C-N bond-forming cross-dehydrogenative couplingof a collectionof Tyr-containing peptides and estrogens with heteroarenes is described.This oxidative coupling is distinguished by its scalability, operationalsimplicity, and air tolerance and enables the appendance of phenothiazinesand phenoxazines in phenol-like compounds. When incorporated intoa Tb(III) metallopeptide, the Tyr-phenothiazine moiety acts as a sensitizerfor the Tb(III) ion, providing a new tool for the design of luminescentprobes.

Automated summary

A cross-dehydrogenative coupling reaction of Tyr-containing peptides and estrogens with heteroarenes was developed, allowing for the formation of C-N bonds. This scalable and air-tolerant oxidative coupling reaction has operational simplicity and enables the attachment of phenothiazines and phenoxazines in phenol-like compounds. Incorporation of the Tyr-phenothiazine moiety into a Tb(III) metallopeptide serves as a sensitizer for the Tb(III) ion, providing a new tool for the design of luminescent probes.