Straightforward Functionalization of Sulfur-Containing Peptides via 5- and 6-endo-dig Cyclization Reactions

Sindija Lapcinska; Pavel Arsenyan

doi:10.1055/a-1343-5607

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(10): 1805-1820
DOI: 10.1055/a-1343-5607

paper

Straightforward Functionalization of Sulfur-Containing Peptides via 5- and 6-endo-dig Cyclization Reactions

Sindija Lapcinska

,

Pavel Arsenyan∗

Abstract

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Abstract

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.

Key words

benzofurans - cysteine - 5-endo-dig - 6-endo-dig - indoles - lipid droplets - peptides - polyaromatic hydrocarbons

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