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Although symmetric macrocyclization strategies have been investigated, non-symmetric stapling of native peptide scaffolds remains underexplored, owing to intricate synthetic challenges associated with achieving concurrent chemoselectivity and site selectivity. This limitation primarily stems from the requirement for orthogonal reactivity in modifying distinct proteinogenic residues while preserving native side-chain functionalities under biocompatible conditions. Herein, a non-symmetric stapling is disclosed for cysteine\u2013lysine (Cys\u2013Lys) crosslinking in unprotected peptides and proteins via unsymmetrically tunable linkers with high chemoselectivity and regioselectivity in a self-assembly manner, in which a library of 17 stapling reagents with adjustable length, angle, flexibility, rigidity and lipophilicity was comprehensively established for relay Cys\u2013Lys ligation, facilitating the macrocyclization of intervening loops (6\u201330 amino acids) into 25\u201340-membered rings under physiologically compatible conditions. The conformationally restricted peptide displayed strengthened \u03b1-helicity, proteolytic stability, serum stability and enhanced anti-bladder cancer activity, demonstrating the potential of this protocol for drug discovery.<\/jats:p>","DOI":"10.1093\/nsr\/nwaf406","type":"journal-article","created":{"date-parts":[[2025,9,20]],"date-time":"2025-09-20T11:50:37Z","timestamp":1758369037000},"source":"Crossref","is-referenced-by-count":7,"title":["Cys\u2013Lys stapling for unprotected peptides via tunable linkers"],"prefix":"10.1093","volume":"12","author":[{"given":"Kaizhen","family":"Miao","sequence":"first","affiliation":[{"name":"Hainan Institute of East China Normal University, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University , Shanghai 200062 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