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Orthogonal bioconjugation targeting cysteine-containing peptides and proteins using alkyl thianthrenium salts.

ABSTRACT: Late-stage specific and selective diversifications of peptides and proteins performed at target residues under ambient conditions are recognized to be the most facile route to various and abundant conjugates. Herein, we report an orthogonal modification of cysteine residues using alkyl thianthreium salts, which proceeds with excellent chemoselectivity and compatibility under mild conditions, introducing a diverse array of functional structures. Crucially, multifaceted bioconjugation is achieved through clickable handles to incorporate structurally diverse functional molecules. This "two steps, one pot" bioconjugation method is successfully applied to label bovine serum albumin. Therefore, our technique is a versatile and powerful tool for late-stage orthogonal bioconjugation.

SUBMITTER: Bao G

PROVIDER: S-EPMC11319714 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Orthogonal bioconjugation targeting cysteine-containing peptides and proteins using alkyl thianthrenium salts.

Bao Guangjun G Song Xinyi X Li Yiping Y He Zeyuan Z Zuo Quan Q E Ruiyao R Yu Tingli T Li Kai K Xie Junqiu J Sun Wangsheng W Wang Rui R

Nature communications 20240812 1

Late-stage specific and selective diversifications of peptides and proteins performed at target residues under ambient conditions are recognized to be the most facile route to various and abundant conjugates. Herein, we report an orthogonal modification of cysteine residues using alkyl thianthreium salts, which proceeds with excellent chemoselectivity and compatibility under mild conditions, introducing a diverse array of functional structures. Crucially, multifaceted bioconjugation is achieved ...[more]

PMID: 39134527

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