Journal
CCS CHEMISTRY
Volume 4, Issue 10, Pages -Publisher
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.021.202101386
Keywords
cyclic peptides; peptide stapling; bioconjugation; chlorooximes; cysteine
Categories
Funding
- National Natural Science Foundation (NSF) of China [21922703, 91953112]
- NSF of Jiangsu Province [BK20190004, BK20202004]
- National Key R&D Program of China [2019YFA0905800]
- Shenzhen Basic Research Program [JCYJ20180508-182240106]
- Fundamental Research Funds for the Central Universities [14380138, 14380131]
- Innovation & Entrepreneurship Talents Plan of Jiangsu Province in China
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Chlorooxime derivatives are cysteine-specific peptide bioconjugation and stapling reagents that can generate stable thiohydroximate linkages, expanding the structural diversity of cyclic peptides.
Cyclic peptides have found applications in fields ranging from drug discovery to nanomaterials. Peptide stapling reagents crosslink two or more residues in peptides to generate macrocycles of diverse topology and introduce linker units that might directly impact the properties and biological functions of cyclic peptides. Herein, we demonstrate that chlorooxime derivatives are cysteine-specific peptide bioconjugation and stapling reagents that generate stable thiohydroximate linkages. In addition, chlorooximes have multiple reaction modes with 1,2-aminothiols and alkynes by generating 4,5-dihydrothiazole and isoxazole motifs, which further expands the structural diversity of cyclic peptides. The high reactivity and chemoselectivity of chlorooximes toward cysteine might support their application in constructing a cyclic peptide library. [GRAPHICS] .
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