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

Guangjun Bao, Xinyi Song, Yiping Li, Zeyuan He, Quan Zuo, Ruiyao E, Tingli Yu, Kai Li, Junqiu Xie (), Wangsheng Sun () and Rui Wang ()
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Guangjun Bao: Chinese Academy of Medical Sciences & Peking Union Medical College
Xinyi Song: Chinese Academy of Medical Sciences & Peking Union Medical College
Yiping Li: Chinese Academy of Medical Sciences & Peking Union Medical College
Zeyuan He: Chinese Academy of Medical Sciences & Peking Union Medical College
Quan Zuo: Chinese Academy of Medical Sciences & Peking Union Medical College
Ruiyao E: Lanzhou University
Tingli Yu: Lanzhou University
Kai Li: Lanzhou University
Junqiu Xie: Chinese Academy of Medical Sciences & Peking Union Medical College
Wangsheng Sun: Chinese Academy of Medical Sciences & Peking Union Medical College
Rui Wang: Chinese Academy of Medical Sciences & Peking Union Medical College

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-51217-9

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