Publication

Ligand-Directed Site-Selective Cysteine Bioconjugation of the KELCH Domain of KEAP1 with Hypervalent Iodine Reagents

2025

Abstract

Affinity-driven reactions have allowed chemists to perform site-selective modifications of native proteins. By combining the high cysteine chemoselectivity of hypervalent iodine-based ethynylbenziodoxolones (EBXs) with the site selectivity of peptide ligands known to inhibit protein−protein interactions, we achieved site-selective labeling of Cys434 in the KELCH domain of Kelch-like epichlorohydrin-associated protein 1 (KEAP1), a key protein in the regulation of oxidative stress. EBXs could be used either as traceless reagents with release of the peptide ligand to introduce reactive handles such as azides or alkynes or as covalent reagents leading to the formation of peptide−protein adducts, which could be cleaved in a separated step.

Official source

https://infoscience.epfl.ch/entities/publication/6a21d2b3-48d7-4a84-b320-13f4ed14eaf3

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2025

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/6a21d2b3-48d7-4a84-b320-13f4ed14eaf3

About this result

Related concepts (32)

Protein

Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, responding to stimuli, providing structure to cells and organisms, and transporting molecules from one location to another. Proteins differ from one another primarily in their sequence of amino acids, which is dictated by the nucleotide sequence of their genes, and which usually results in protein folding into a specific 3D structure that determines its activity.

Peptide

Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides which have a molecular mass of 10,000 Da or more are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides. Peptides fall under the broad chemical classes of biological polymers and oligomers, alongside nucleic acids, oligosaccharides, polysaccharides, and others.

Native state

In biochemistry, the native state of a protein or nucleic acid is its properly folded and/or assembled form, which is operative and functional. The native state of a biomolecule may possess all four levels of biomolecular structure, with the secondary through quaternary structure being formed from weak interactions along the covalently-bonded backbone. This is in contrast to the denatured state, in which these weak interactions are disrupted, leading to the loss of these forms of structure and retaining only the biomolecule's primary structure.

Related publications (32)

Ligand-Directed Site-Selective Cysteine Bioconjugation of the KELCH Domain of KEAP1 with Hypervalent Iodine Reagents

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