{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Kumar GS"],"funding":["National Institute of General Medical Sciences","NIGMS NIH HHS","NIH HHS"],"pagination":["57-62"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8982153"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["144(1)"],"pubmed_abstract":["Here we report the design of a superfast bioorthogonal ligation reactant pair comprising a sterically shielded, sulfonated tetrazole and bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN). The design involves placing a pair of water-soluble <i>N</i>-sulfonylpyrrole substituents at the C-phenyl ring of diphenyltetrazoles to favor the photoinduced cycloaddition reaction over the competing nucleophilic additions. First-principles computations provide vital insights into the origin of the tetrazole-BCN cycloaddition's superior kinetics compared to the tetrazole-spirohexene cycloaddition. The tetrazole-BCN cycloaddition also enabled rapid bioorthogonal labeling of glucagon receptors on live cells in as little as 15 s."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Superfast Tetrazole-BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells."],"pmcid":["PMC8982153"],"funding_grant_id":["R35 GM130307","R35GM130307","S10 OD024973"],"pubmed_authors":["Lin Q","Kumar GS","Racioppi S","Zurek E"],"additional_accession":[]},"is_claimable":false,"name":"Superfast Tetrazole-BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells.","description":"Here we report the design of a superfast bioorthogonal ligation reactant pair comprising a sterically shielded, sulfonated tetrazole and bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN). The design involves placing a pair of water-soluble <i>N</i>-sulfonylpyrrole substituents at the C-phenyl ring of diphenyltetrazoles to favor the photoinduced cycloaddition reaction over the competing nucleophilic additions. First-principles computations provide vital insights into the origin of the tetrazole-BCN cycloaddition's superior kinetics compared to the tetrazole-spirohexene cycloaddition. The tetrazole-BCN cycloaddition also enabled rapid bioorthogonal labeling of glucagon receptors on live cells in as little as 15 s.","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Jan","modification":"2025-04-19T13:31:34.914Z","creation":"2025-04-19T13:31:34.914Z"},"accession":"S-EPMC8982153","cross_references":{"pubmed":["34964645"],"doi":["10.1021/jacs.1c10354"]}}