{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Page ACS"],"funding":["NIEHS NIH HHS","Mark Foundation For Cancer Research","National Institutes of Health"],"pagination":["3851-3856"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8966736"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["13(13)"],"pubmed_abstract":["Photoaffinity labeling (PAL) is a powerful tool for the identification of non-covalent small molecule-protein interactions that are critical to drug discovery and medicinal chemistry, but this approach is limited to only a small subset of robust photocrosslinkers. The identification of new photoreactive motifs capable of covalent target capture is therefore highly desirable. Herein, we report the design, synthesis, and evaluation of a new class of PAL warheads based on the UV-triggered 1,2-photo-Brook rearrangement of acyl silanes, which hitherto have not been explored for PAL workflows. Irradiation of a series of probes in cell lysate revealed an <i>i</i>Pr-substituted acyl silane with superior photolabeling and minimal thermal background labeling compared to other substituted acyl silane"],"journal":["Chemical science"],"pubmed_title":["Photo-Brook rearrangement of acyl silanes as a strategy for photoaffinity probe design."],"pmcid":["PMC8966736"],"funding_grant_id":["P42 ES004705","R01GM136945","P42ES004705","R01CA240981"],"pubmed_authors":["Belcher BP","Toste FD","Nomura DK","Keenan KN","Schirle M","Scholz SO","Tallarico JA","McKenna JM","Brittain SM","Page ACS","Spradlin JN"],"additional_accession":[]},"is_claimable":false,"name":"Photo-Brook rearrangement of acyl silanes as a strategy for photoaffinity probe design.","description":"Photoaffinity labeling (PAL) is a powerful tool for the identification of non-covalent small molecule-protein interactions that are critical to drug discovery and medicinal chemistry, but this approach is limited to only a small subset of robust photocrosslinkers. The identification of new photoreactive motifs capable of covalent target capture is therefore highly desirable. Herein, we report the design, synthesis, and evaluation of a new class of PAL warheads based on the UV-triggered 1,2-photo-Brook rearrangement of acyl silanes, which hitherto have not been explored for PAL workflows. Irradiation of a series of probes in cell lysate revealed an <i>i</i>Pr-substituted acyl silane with superior photolabeling and minimal thermal background labeling compared to other substituted acyl silane","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Mar","modification":"2025-04-04T10:44:35.526Z","creation":"2025-04-04T10:44:35.526Z"},"accession":"S-EPMC8966736","cross_references":{"pubmed":["35432890"],"doi":["10.1039/d2sc00426g"]}}