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Updated: Jul 4, 2026
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
[Fmoc solid-phase synthesis of cyclopeptide FIK]
Junjun Zhang1, Wei Shi, Wuling Chen
1College of Life Science, Northwest University, Xi'an 710069, China.
Summary
Researchers developed an efficient solid-phase synthesis for disulfide-bonded cyclopeptides. This method yields high-purity cyclic peptides suitable for large-scale production.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Biochemistry
Context:
- Cyclic peptides containing disulfide bonds are crucial in drug discovery and biological studies.
- Traditional synthesis methods can be complex and low-yielding.
- Developing efficient and scalable synthesis techniques is essential.
Purpose:
- To establish a robust and straightforward method for synthesizing disulfide-bond-bearing cyclopeptides.
- To optimize solid-phase synthesis conditions for cyclopeptide formation.
- To evaluate the yield and purity of the synthesized cyclic peptides.
Summary:
- The study utilized Fmoc-amino acid chemistry and solid-phase synthesis (SPPS) with HBTU/HOBt/DIEA for linear peptide construction.
- Intramolecular disulfide bonds were formed via iodine oxidation of bis-cysteine residues in the linear peptide.
- The resulting cyclopeptides were cleaved, purified by RP-HPLC, and characterized using MALDI-MS and Ellman's reagent, achieving >97% purity and 18% yield.
Impact:
- The developed method is effective, simple, and rapid, offering good yields.
- This technique is suitable for the large-scale production of disulfide-bonded cyclopeptides.
- The findings contribute to advancing the synthesis of complex cyclic peptide therapeutics.
