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JoVE Journal
Chemistry
Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
JoVE Journal
Chemistry
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JoVE Journal Chemistry
Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Full Text
3,165 Views
07:11 min
September 28, 2022

DOI: 10.3791/64289-v

Chunli Song*1, Zhanfeng Hou*1,2, Zijun Jiao*1, Zhaodi Liu3, Chenshan Lian1,2, Min Zhang1, Wei Liang3, Feng Yin1,2, Zigang Li1,2

1Pingshan Translational Medicine Center,Shenzhen Bay Laboratory, 2Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology,Peking University Shenzhen Graduate School, 3Department of Radiation Oncology, the First Affiliated Hospital,Anhui Medical University

This protocol presents the synthesis of cyclic peptides via bisalkylation between cysteine and methionine and the facile thiol-yne reaction triggered by the propargyl sulfonium center.

In this protocol, the sulfonium salt was constructed that could act as a new hand that reacted with the protein cysteine on the special proximity. The advantage of this technique was that this reaction was fast and efficient, and Met-catalyst free and developed a simple and efficient method for stabilizing peptides. To begin, prepare the N-terminal 9-fluorinyl-methyloxycarbonyl deprotection solution of 20%piperidine or 50%morpholine and DMF in a 500-milliliter beaker or flask.

Then, add 10 milliliters of the deprotection solution to the column and bubbled nitrogen into the solution for 30 minutes or twice for five minutes. Drain the solution by a vacuum pump and wash the resin sequentially for five times with dichloromethane and N, N-dimethylformamide. To detect the resin as a darky yellow color solution, add one milliliter of N, N-dimethylformamide to a small amount of resin and add 200 microliters of 5%ninhydrin to a glass tube.

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