Straightforward Functionalization of Sulfur-Containing Peptides via 5- And 6- endo - Dig Cyclization Reactions

Synthesis 2021
Sindija Lapčinska, P Arsenyan

We present a simple and convenient method for the generation of sulfenyl electrophiles from peptides containing S-S or S-H bonds by employing N -chlorosuccinimide. The corresponding sulfenyl electrophiles are further utilized in 5- and 6- endo - dig cyclization reactions yielding indolizinium salts, indoles, benzo[ b ]furans, polyaromatic hydrocarbons (PAHs) and isocoumarins, as well as quinolinones bearing a glutathione moiety. PAH derivatives can be used as selective fluorescent dyes for the visualization of lipid droplets in living cells.

Atslēgas vārdi
5- endo - dig | 6- endo - dig | benzofurans | cysteine | indoles | lipid droplets | peptides | polyaromatic hydrocarbons
DOI
10.1055/a-1343-5607
Hipersaite
https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-1343-5607

Lapčinska, S., Arsenyan, P. Straightforward Functionalization of Sulfur-Containing Peptides via 5- And 6- endo - Dig Cyclization Reactions. Synthesis, 2021, Vol. 53, No. 10, 1805.-1820.lpp. ISSN 0039-7881. e-ISSN 1437-210X. Pieejams: doi:10.1055/a-1343-5607

Publikācijas valoda
English (en)