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

Autor: Girón-Elola C; University of the Basque Country (UPV/EHU), Department of Organic Chemistry I, Joxe Mari Korta R&D Center, Avda. Tolosa 72, 20018 Donostia-San Sebastián, Spain., Sasiain I; University of the Basque Country (UPV/EHU), Department of Organic Chemistry I, Joxe Mari Korta R&D Center, Avda. Tolosa 72, 20018 Donostia-San Sebastián, Spain., Sánchez-Fernández R; CICA - Centro Interdisciplinar de Química e Bioloxía and Departamento de Química, Facultade de Ciencias, Universidade da Coruña, Campus de Elviña, 15071 A Coruña, Spain., Pazos E; CICA - Centro Interdisciplinar de Química e Bioloxía and Departamento de Química, Facultade de Ciencias, Universidade da Coruña, Campus de Elviña, 15071 A Coruña, Spain., Correa A; University of the Basque Country (UPV/EHU), Department of Organic Chemistry I, Joxe Mari Korta R&D Center, Avda. Tolosa 72, 20018 Donostia-San Sebastián, Spain.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2023 Jun 16; Vol. 25 (23), pp. 4383-4387. Date of Electronic Publication: 2023 Jun 07.
DOI: 10.1021/acs.orglett.3c01560
Abstrakt: A C-N bond-forming cross-dehydrogenative coupling of a collection of Tyr-containing peptides and estrogens with heteroarenes is described. This oxidative coupling is distinguished by its scalability, operational simplicity, and air tolerance and enables the appendance of phenothiazines and phenoxazines in phenol-like compounds. When incorporated into a Tb(III) metallopeptide, the Tyr-phenothiazine moiety acts as a sensitizer for the Tb(III) ion, providing a new tool for the design of luminescent probes.
Databáze: MEDLINE