Fast and Selective Cysteine Conjugation Using <i>para</i>-Quinone Methides
An efficient and selective method for cysteine conjugation utilizing <i>para</i>-quinone methides (<i>p</i>-QMs) was developed. <i>p</i>-QM labeling exhibits high specificity toward the cysteine residue, as evidenced by its reactivity with various amino acid derivatives, peptides, and proteins. Notably, the <i>p</i>-QM-cysteine reactions display robust kinetics with rate constants up to 1.67 × 10<sup>4</sup> M<sup>-1</sup>·s<sup>-1</sup>. Furthermore, <i>p</i>-QM conjugation enables us to attach a fluorescent probe to a HER2 nanobody, resulting in selective labeling of HER2-positive SK-BR-3 cells.
Authors
- Shang Gao (ORCID: https://orcid.org/0000-0001-8166-5503)
- Aijun Lin (ORCID: https://orcid.org/0000-0001-5786-4537)
- Liuli Dong
- Xiaoxing Wu (ORCID: https://orcid.org/0000-0003-3378-1299)
- Zhaoliang Hu (ORCID: https://orcid.org/0000-0002-3222-9235)
- Taijun Hang (ORCID: https://orcid.org/0000-0002-3057-4705)
- Qian Chu (ORCID: https://orcid.org/0000-0001-6550-6975)
- Xue Li (ORCID: https://orcid.org/0000-0003-4836-7808)
- Ruimin Zhang (ORCID: https://orcid.org/0000-0001-9354-0169)
- Bo Li (ORCID: https://orcid.org/0009-0001-4607-5329)
- Jia Zheng
- Xueyu Yao
Institutions
- China Pharmaceutical University (CN)
- Shimadzu (China) (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-07
- DOI
- https://doi.org/10.1021/acs.orglett.4c03452
- Citations
- 5
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- National Natural Science Foundation of China
- China Pharmaceutical University
- Natural Science Foundation of Jiangsu Province
- Fundamental Research Funds for the Central Universities