Metal-Free Late-Stage Alkylation of Tryptophan and Tryptophan-Containing Peptides with 1,3-Dithiane Derivatives

Abstract

Published as part of the Organic Letters virtual special issue "Chemoselective Methods for Labeling and Modification of Peptides and Proteins".

Photoredox C(2)-Arylation of Indole- and Tryptophan-Containing Biomolecules

“…Current strategies for the selective modification of Trp often rely on transition-metal-catalyzed C–H activation reactions, − although several metal-free approaches have also been reported. − It is noteworthy, however, that many of these methods involve intricate reaction mixtures or necessitate the use of harsh conditions, such as elevated temperatures, thereby limiting their application in more sensitive systems.…”

Synthesis of β,β-Dithioketones by Merging C–C and C–S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation

“…Owing to the special redox properties and outstanding reactivity of sulfur atoms, sulfur-containing compounds are widely used in the fields of medicine, pesticides, materials science, and organic chemistry . As an important sulfur-containing organic building block, 1,3-dithiane is typically used as a C1 unit or masked carbonyl equivalent , and has a wide range of applications in natural products construction and synthetic methodology . Besides, 1,3-dithiane derivatives reportedly exhibit insecticidal activity and good chemical stability .…”