{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Taylor KI"],"funding":["National Institute of Allergy and Infectious Diseases","NIAID NIH HHS","National Institute of General Medical Sciences","NIGMS NIH HHS","Division of Graduate Education"],"pagination":["25056-25060"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10935565"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["145(46)"],"pubmed_abstract":["Probes that covalently label protein targets facilitate the identification of ligand-binding sites. Lysine residues are prevalent in the proteome, making them attractive substrates for covalent probes. However, identifying electrophiles that undergo amine-specific, regioselective reactions with binding site lysine residues is challenging. Squarates can engage in two sequential conjugate addition-elimination reactions with amines. Nitrogen donation reduces the second reaction rate, making the mono squaramide a mild electrophile. We postulated that this mild electrophilicity would demand a longer residence time near the amine, affording higher selectivity for binding site lysines. Therefore, we compared the kinetics of squarate and monosquaramide amine substitution to alternative amine bioco"],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Assessing Squarates as Amine-Reactive Probes."],"pmcid":["PMC10935565"],"funding_grant_id":["R01 AI126592","F31 GM148069","AI-R01 126592","2019281534"],"pubmed_authors":["Kiessling LL","Ho JS","Carter AW","Taylor KI","Trial HO"],"additional_accession":[]},"is_claimable":false,"name":"Assessing Squarates as Amine-Reactive Probes.","description":"Probes that covalently label protein targets facilitate the identification of ligand-binding sites. Lysine residues are prevalent in the proteome, making them attractive substrates for covalent probes. However, identifying electrophiles that undergo amine-specific, regioselective reactions with binding site lysine residues is challenging. Squarates can engage in two sequential conjugate addition-elimination reactions with amines. Nitrogen donation reduces the second reaction rate, making the mono squaramide a mild electrophile. We postulated that this mild electrophilicity would demand a longer residence time near the amine, affording higher selectivity for binding site lysines. Therefore, we compared the kinetics of squarate and monosquaramide amine substitution to alternative amine bioco","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Nov","modification":"2026-06-03T07:25:06.49Z","creation":"2025-04-06T10:11:24.821Z"},"accession":"S-EPMC10935565","cross_references":{"pubmed":["37938802"],"doi":["10.1021/jacs.2c05691"]}}