Visible Light-Mediated Functionalization of Selenocystine-Containing Peptides
Advanced Synthesis and Catalysis 2021
Sindija Lapčinska, Pavels Dimitrijevs, Linards Lapčinskis, Pavel Arsenyan

A straightforward and atom-economic method for the functionalization of short selenocystine-containing peptides is presented. This method is shown to be tolerant to unprotected peptides. The detailed protocol is based on the generation of a selenium radical via visible light-initiated reaction in the presence of transition metal-free photocatalyst. The selenium radical is further oxidized to an electrophile and trapped by N-heterocycles. The mechanism is confirmed by NMR, HRMS, UV, EPR and cyclic voltammetry (CV) experiments and photocatalyst emission quenching studies. A visible light-initiated reaction is employed for the synthesis of selenocysteine-containing indole-based macrocycles via intramolecular Se−C bond formation.


DOI
10.1002/adsc.202100373
Hyperlink
https://onlinelibrary.wiley.com/doi/10.1002/adsc.202100373

Lapčinska, S., Dimitrijevs, P., Lapčinskis, L., Arsenyan, P. Visible Light-Mediated Functionalization of Selenocystine-Containing Peptides. Advanced Synthesis and Catalysis, 2021, Vol. 363, No. 13, pp.3318-3328. ISSN 1615-4150. e-ISSN 1615-4169. Available from: doi:10.1002/adsc.202100373

Publication language
English (en)
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