Efficient and simple synthesis of polypeptide compounds containing two pairs of disulfide bonds

doi:10.7503/cjcu20250233

Chem. J. Chinese Universities

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Efficient and simple synthesis of polypeptide compounds containing two pairs of disulfide bonds

ZHANG Bin^1,2, DAI Xiandong¹, MENG Fanhua¹, LI Yulong², LV Zirui¹

1. State Key Laboratory of Chemistry for NBS Hazards Protection 2. Sichuan University of Science & Engineering，College of Chemical and Environmental Engineering

Received:2025-08-25 Revised:2025-10-10 Online First:2025-10-15 Published:2025-10-15
Contact: Zi-Rui LV E-mail:lvzirui@sklnbcpc.cn
Supported by:
Supported by the National Natural Science Foundation of China (No. 22373056) and the Scientific Research and Innovation Team Program of Sichuan University of Science and Engineering (No. SUSE652A014)

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Abstract

Abstract: Using triphenylmethyl (Trt) and acetaminomethyl (Acm) as the protective groups of the cysteine thiol side chain, and H2O2 and I2 as oxidants respectively, through the optimization of reaction conditions, the "one-pot" step-by-step precise synthesis of polypeptide compounds containing two pairs of disulfide bonds was achieved. This reaction strategy does not require purification of the intermediate products, is easy to operate, and has a fast reaction rate. The two pairs of disulfide bonds in the polypeptide were completely constructed within 20 minutes. The research results show that this reaction strategy has wide substrate applicability. A series of biologically active peptide compounds, including those containing tryptophan and methionine, were obtained by adopting this strategy with high overall yields.

Key words: Disulfide bond, One-pot method, Precision, Efficient, Synthesis

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ZHANG Bin, DAI Xiandong, MENG Fanhua, LI Yulong, LV Zirui. Efficient and simple synthesis of polypeptide compounds containing two pairs of disulfide bonds[J]. Chem. J. Chinese Universities, doi: 10.7503/cjcu20250233.

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Efficient and simple synthesis of polypeptide compounds containing two pairs of disulfide bonds

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