A kinetic study of thiol addition to

Sulfhydryl Compounds / chemistry Cysteine / chemistry Acetamides / pharmacology Models, Molecular Kinetics

Journal

Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995

Informations de publication

Date de publication:
07 06 2023
Historique:
medline: 8 6 2023
pubmed: 25 5 2023
entrez: 25 5 2023
Statut: epublish

Résumé

Irreversible enzyme inhibitors bind covalently to their target and permanently limit its function. The redox-sensitive thiol group on the side chain of cysteine (Cys) residues is often the nucleophilic group that is targeted for reaction with the electrophilic warhead of irreversible inhibitors. While the acrylamide group is the warhead applied most frequently currently in the design of inhibitors with therapeutic potential, the chloroacetamide group offers a comparable reactivity profile. In that context, we have studied the details of the mechanism of thiol addition to

Identifiants

DOI: 10.1039/d3ob00523b PMID: 37227378
pubmed: 37227378
doi: 10.1039/d3ob00523b
doi:

Substances chimiques

Sulfhydryl Compounds 0
chloroacetamide 2R97846T1L
Cysteine K848JZ4886
Acetamides 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

4702-4710

Auteurs

Sarah K I Watt (SKI)

Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Canada. jkeillor@uottawa.ca.

Janique G Charlebois (JG)

Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Canada. jkeillor@uottawa.ca.

Christopher N Rowley (CN)

Department of Chemistry, Carleton University, Ottawa, Canada.
ORCID: 0000-0002-0205-952X

Jeffrey W Keillor (JW)

Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Canada. jkeillor@uottawa.ca.
ORCID: 0000-0002-8133-6862

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Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Composés du soufre › Thiols › A kinetic study of thiol addition to
questionsmedicales.fr › Acides aminés, peptides et protéines › Acides aminés › Acides aminés soufrés › Cystéine › A kinetic study of thiol addition to
questionsmedicales.fr › Composés chimiques organiques › Acides carboxyliques › Acides acycliques › Acétamides › A kinetic study of thiol addition to
questionsmedicales.fr › Techniques d'investigation › Modèles théoriques › Modèles moléculaires › A kinetic study of thiol addition to
questionsmedicales.fr › Phénomènes chimiques › Phénomènes biochimiques › Cinétique › A kinetic study of thiol addition to