Cu-catalyzed alkynylation of thiosulfonate-based peptide: an efficient approach to S-alkynyl-containing cyclic peptides - Details

author：

Zhang, Zhou (Zhang, Zhou.) ^[1] | Ying, Junjie (Ying, Junjie.) ^[2] | Lu, Qingqing (Lu, Qingqing.) ^[3] | Zhang, Qinshuo (Zhang, Qinshuo.) ^[4] | Xu, Chunfa (Xu, Chunfa.) ^[5]

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Abstract：

Cyclic　peptides　are　highly　valued　in　drug　discovery　due　to　their　enhanced　biological　properties.　Despite　their　potential,　the　construction　of　an　S-alkynyl　moiety　in　a　cyclic　peptide　remains　challenging　due　to　limited　synthetic　strategies.　Herein,　we　describe　a　copper-catalyzed　alkynylation　of　thiosulfonate-based　peptides,　enabling　efficient　and　selective　synthesis　of　S-alkynylated　cysteines　and　peptides.　The　adjustment　of　the　amount　of　base　could　significantly　increase　the　efficiency.　This　method　features　a　broad　substrate　scope,　operational　simplicity　and　compatibility　with　complex　peptide　structures.　©　2025　The　Royal　Society　of　Chemistry.

Keyword：

Alkylation Alkynes Catalysis

Community：

[ 1 ] [Zhang, Zhou]Key Laboratory of Molecular Synthesis and Functionalization Discovery, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 2 ] [Ying, Junjie]Key Laboratory of Molecular Synthesis and Functionalization Discovery, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 3 ] [Lu, Qingqing]Key Laboratory of Molecular Synthesis and Functionalization Discovery, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 4 ] [Zhang, Qinshuo]Key Laboratory of Molecular Synthesis and Functionalization Discovery, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 5 ] [Xu, Chunfa]Key Laboratory of Molecular Synthesis and Functionalization Discovery, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 6 ] [Xu, Chunfa]Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai; 200032, China

Reprint 's Address：

[xu, chunfa]key laboratory of molecular synthesis and functionalization discovery, college of chemistry, fuzhou university, fuzhou; 350108, china;;[xu, chunfa]key laboratory of organofluorine chemistry, shanghai institute of organic chemistry, cas, shanghai; 200032, china

Email：

xucf@fzu.edu.cn

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Source ：

Organic Chemistry Frontiers

ISSN： 2052-4110

Year： 2025

Issue： 8

Volume： 12

Page： 2752-2758

4 . 6 0 0

JCR@2023

CAS Journal Grade：2

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ESI Highly Cited Papers on the List： 0 Unfold All

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