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Updated: Jun 5, 2025

07:11
Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
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Non-symmetric cysteine stapling in native peptides and proteins
Sven Ullrich1, Bishvanwesha Panda1, Upamali Somathilake1
1Research School of Chemistry, College of Science, Australian National University, Canberra 2601 ACT, Australia. sullrich@g.ecc.u-tokyo.ac.jp.
Abstract:
Stapling rigidifies peptides through covalent linkages between amino acids. We introduce 2-chloromethyl-6-cyanopyridine for non-symmetric stapling of N-terminal and internal cysteines. This biocompatible method produces diverse peptide macrocycles with enhanced affinity, stability and inhibitory potency. It is applicable to native peptides and proteins alike, demonstrating potential for peptide drug discovery platforms.

