We report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor-acceptor complex generated between the tryptophan unit and pyridinium salts. Irradiation with weak light (390 nm) generates radical intermediates right next to the targeted Trp amino acid, facilitating a proximity-driven radical functionalization. This protocol exhibits high chemoselectivity for Trp residues over other amino acids and tolerates biocompatible conditions.

Photochemical Chemoselective Alkylation of Tryptophan-Containing Peptides

Melchiorre P.
Ultimo
Supervision
2021

Abstract

We report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor-acceptor complex generated between the tryptophan unit and pyridinium salts. Irradiation with weak light (390 nm) generates radical intermediates right next to the targeted Trp amino acid, facilitating a proximity-driven radical functionalization. This protocol exhibits high chemoselectivity for Trp residues over other amino acids and tolerates biocompatible conditions.
2021
Laroche B.; Tang X.; Archer G.; Di Sanza R.; Melchiorre P.
File in questo prodotto:
File Dimensione Formato  
ol-2020-037356_revised.pdf

Open Access dal 06/01/2022

Tipo: Postprint
Licenza: Licenza per Accesso Aperto. Altra tipologia di licenza compatibile con Open Access
Dimensione 1.35 MB
Formato Adobe PDF
1.35 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/897866
Citazioni
  • ???jsp.display-item.citation.pmc??? 6
  • Scopus 25
  • ???jsp.display-item.citation.isi??? 28
social impact