Fast and Selective Cysteine Conjugation Using para-Quinone Methides

被引：1

作者：

Zhang, Ruimin ^{[1
]}

Li, Bo ^{[1
]}

Dong, Liuli ^{[1
]}

Hu, Zhaoliang ^{[1
]}

Li, Xue ^{[1
]}

Yao, Xueyu ^{[1
]}

Zheng, Jia ^{[2
]}

Lin, Aijun ^{[1
]}

Gao, Shang ^{[1
]}

Hang, Taijun ^{[3
]}

Wu, Xiaoxing ^{[4
]}

Chu, Qian ^{[4
]}

机构：

[1] China Pharmaceut Univ, Sch Pharm, Nanjing 211198, Peoples R China

[2] Shimadzu China Co Ltd, Shanghai 200233, Peoples R China

[3] China Pharmaceut Univ, Sch Pharm, Dept Pharmaceut Anal, Nanjing 211198, Peoples R China

[4] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 211198, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 41期

基金：

中国国家自然科学基金;

关键词：

PROTEINS; CELLS;

D O I：

10.1021/acs.orglett.4c03452

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and selective method for cysteine conjugation utilizing para-quinone methides (p-QMs) was developed. p-QM labeling exhibits high specificity toward the cysteine residue, as evidenced by its reactivity with various amino acid derivatives, peptides, and proteins. Notably, the p-QM-cysteine reactions display robust kinetics with rate constants up to 1.67 x 10(4) M-1<middle dot>s(-1). Furthermore, p-QM conjugation enables us to attach a fluorescent probe to a HER2 nanobody, resulting in selective labeling of HER2-positive SK-BR-3 cells.

引用

页码：8951 / 8955

页数：5

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