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
Financial support from the Latvijas Organiskās sintēzes institūts (Latvian Institute of Organic Synthesis) is gratefully acknowledged (internal grant: IG-2020-07).


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.

Supporting Information



Publication History

Received: 23 November 2020

Accepted after revision: 28 December 2020

Publication Date:
28 December 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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