Application of Thiol-yne/Thiol-ene Reactions for Peptide and Protein Macrocyclizations.

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ID: 14388
2017
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Ranked #86 of 117 articles by views in Chemistry (Weinheim an der Bergstrasse, Germany)

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Abstract
The application of thiol-yne/thiol-ene reactions to synthesize mono- and bicyclic-stapled peptides and proteins is reported. First, a thiol-ene-based peptide-stapling method in aqueous conditions was developed. This method enabled the efficient stapling of recombinantly expressed coil-coiled proteins. The resulting stapled protein demonstrated higher stability in its secondary structure than the unstapled version. Furthermore, a thiol-yne coupling was performed by using an α,ω-diyne to react with two cysteine residues to synthesize a stapled peptide with two vinyl sulfide groups. The stapled peptide could further react with another biscysteine peptide to yield a bicyclic stapled peptide with enhanced properties. For example, the cell permeability of a stapled peptide was further increased by appending an oligoarginine cell-penetrating peptide. The robustness and versatility of thiol-yne/thiol-ene reactions that can be applied to both synthetic and expressed peptides and proteins were demonstrated.
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wang2017applicationchemistry Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Wang, Yuanxiang;Bruno, Benjamin J;Cornillie, Sean;Nogieira, Jason M;Chen, Diao;Cheatham, Thomas E;Lim, Carol S;Chou, Danny Hung-Chieh;
Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Year 2017
DOI
10.1002/chem.201700572
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