Peptide Functionalization through the Generation of Selenocysteine Electrophile

European Journal of Organic Chemistry 2019
P. Arsenyan, Sindija Lapčinska, A. Ivanova, J. Vasiljeva

Herein we report the first example of a strategy for peptide functionalization through the generation of selenocysteine electrophile in 5- and 6-endo-dig cyclization reactions. This simple approach allows bio-conjugation of selenocystine-based peptides. The developed protocol is based on copper(II) bromide mediated reactions of selenocystine with either 2-propargyl N-heterocycles through 5-endo-dig closure or with 2-ethynylbiaryls through 6-endo-dig closure. It allows construction of indolizinium moiety on selenocysteine residue as well as formation of polyaromatic fragment bonded to selenium in a simple one-pot process under mild reaction conditions.

Atslēgas vārdi
5-endo-dig, 6-endo-dig, Diselenide, Peptides, Selenocysteine
DOI
10.1002/ejoc.201900907
Hipersaite
https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201900907

Arsenyan, P., Lapčinska, S., Ivanova, A., Vasiljeva, J. Peptide Functionalization through the Generation of Selenocysteine Electrophile. European Journal of Organic Chemistry, 2019, Vol. 2019, No. 30, 4951.-4961.lpp. ISSN 1434-193X. Pieejams: doi:10.1002/ejoc.201900907

Publikācijas valoda
English (en)