Convergent Synthesis of Thioether Containing Peptides

Abstract

Thioether containing peptides were obtained following three synthetic routes. In route A, halo acids esterified on 2-chlorotrityl(Cltr) resin were reacted with N-fluorenylmethoxycarbonyl (Fmoc) aminothiols. These were either cleaved from the resin to the corresponding (Fmoc-aminothiol)carboxylic acids, which were used as key building blocks in solid phase peptide synthesis (SPPS), or the N-Fmoc group was deprotected and peptide chains were elongated by standard SPPS. The obtained N-Fmoc protected thioether containing peptides were then condensed either in solution, or on solid support, with the appropriate amino components of peptides. In route B, the thioether containing peptides were obtained by the reaction of N-Fmoc aminothiols with bromoacetylated peptides, which were synthesized on Cltr-resin, followed by removal of the N-Fmoc group and subsequent peptide elongation by standard SPPS. In route C, the thioether containing peptides were obtained by the condensation of a haloacylated peptide synthesized on Cltr-resin and a thiol-peptide synthesized either on 4-methoxytrityl(Mmt) or trityl(Trt) resin.

Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation

“…Aryl sulfides, as a ubiquitous structural motif in functional molecules, plays a unique role in pharmaceutical ( Le Grand et al, 2008 ; Ilardi et al, 2014 ; Xiao et al, 2019 ; Golosov et al, 2021 ; Mourtas et al, 2020 ; Hai et al, 2021 ; Liu and Jiang, 2013 ; Barce Ferro et al, 2020 ) and material science ( Figure 1 ). ( Boyd 2016 ; Lu et al, 2017 ; Zhang et al, 2018 ; Hou et al, 2022 ) Hence, the development of efficient methods for the construction of C-S bond has attracted considerable attentions from chemical researchers.…”