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

Area of Science:

• Organic Chemistry
• Biochemistry
• Materials Science

Background:

• Cross-dehydrogenative coupling reactions are crucial for C-N bond formation.
• Peptide and estrogen functionalization is important for developing new molecular tools.
• Developing efficient and scalable synthetic methods is a key challenge in organic chemistry.

Purpose of the Study:

• To develop a novel C-N bond-forming cross-dehydrogenative coupling reaction.
• To functionalize tyrosine-containing peptides and estrogens with heteroarenes.
• To create novel luminescent probes using the synthesized compounds.

Main Methods:

• Oxidative coupling of tyrosine-containing peptides and estrogens with heteroarenes.
• Appendance of phenothiazines and phenoxazines to phenol-like compounds.
• Incorporation of the functionalized moiety into a terbium(III) (Tb(III)) metallopeptide.

Main Results:

• A scalable, operationally simple, and air-tolerant C-N bond-forming cross-dehydrogenative coupling reaction was established.
• Phenothiazine and phenoxazine moieties were successfully appended to phenol-like compounds.
• The Tyr-phenothiazine moiety in a Tb(III) metallopeptide demonstrated sensitizer properties for Tb(III) luminescence.

Conclusions:

• The developed method provides an efficient route for synthesizing functionalized peptides and estrogens.
• The synthesized compounds can serve as effective sensitizers in luminescent probes.
• This work offers a new strategy for designing advanced luminescent materials and probes.