Mild Lewis-Acid-Promoted Cysteine-Tryptophan Conjugation Involving a Radical Process - Details

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Numerous　methods　have　been　developed　for　peptide　synthesis　due　to　their　great　potential　in　drug　discovery.　However,　the　technique　for　tryptophan-cysteine　conjugation　is　still　underexplored.　Herein,　we　present　a　TMSBr-promoted　ligation　of　tryptophan　and　cysteine　under　mild　conditions　by　using　a　sulfonate-modified　cysteine　substrate.　This　protocol　features　a　broad　scope　and　high　site　selectivity　and　is　applicable　for　synthesis　of　cyclic　peptide.　Preliminary　mechanistic　studies　reveal　that　the　reaction　proceeds　via　a　radical　process.　©　2025　American　Chemical　Society.

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[ 1 ] [Lu Q.]Key Laboratory of Molecular Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 2 ] [Wen H.]Key Laboratory of Molecular Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 3 ] [Zhang Q.]Key Laboratory of Molecular Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 4 ] [Zhang Z.]Key Laboratory of Molecular Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 5 ] [Wang S.]College of Chemical Engineering, Fuzhou University, Fuzhou, 350108, China
[ 6 ] [Wang R.]Shengli Clinical Medical College of Fujian Medical University, Department of Breast Surgery, Fujian Provincial Hospital, Fuzhou University Affiliated Provincial Hospital, Fuzhou University, Fuzhou, 350001, China
[ 7 ] [Xu C.]Key Laboratory of Molecular Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 8 ] [Xu C.]Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

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Organic Letters

ISSN： 1523-7060

Year： 2025

Issue： 23

Volume： 27

Page： 6192-6197

4 . 9 0 0

JCR@2023

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