{"doi":"10.1021/jacs.4c04141","title":"A Method for Rigorously Selective Capture and Simultaneous Fluorescent Labeling of N-Terminal Glycine Peptides","abstract":"Although chemical methods for the selective derivatization of amino acid (AA) side chains in peptides and proteins are available, selective N-terminal labeling is challenging, especially for glycine, which has no side chain at the α-carbon position. We report here a double activation at glycine's α-methylene group that allows this AA to be differentiated from the other 19 AAs. A condensation reaction of dibenzoylmethane with glycine results in the formation of an imine, and subsequent tautomerization is followed by intramolecular cyclization, leading to the formation of a fluorescent pyrrole ring. Additionally, the approach exhibits compatibility with AAs possessing reactive side chains. Further, the method allows for selective pull-down assays of N-terminal glycine peptides from mixtures without prior knowledge of the N-terminal peptide distribution.","journal":"Journal of the American Chemical Society","year":2024,"id":435246,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":12,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.954,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2024-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1242416,"name":"Harnimarta Deol","orcid":"0000-0003-2798-564X","position":1,"is_corresponding":false},{"id":1242881,"name":"Ava Raeisbahrami","orcid":null,"position":2,"is_corresponding":false},{"id":1242882,"name":"Hadis Askari","orcid":null,"position":3,"is_corresponding":false},{"id":867047,"name":"Christopher D. Wight","orcid":"0000-0003-3389-1762","position":4,"is_corresponding":false},{"id":391290,"name":"Vincent M. Lynch","orcid":"0000-0002-5260-9913","position":5,"is_corresponding":false},{"id":301811,"name":"Eric V. Anslyn","orcid":"0000-0002-5137-8797","position":6,"is_corresponding":false},{"id":680469,"name":"Hongxu Liu","orcid":"0000-0003-0076-1259","position":0,"is_corresponding":true}],"reference_count":43,"raw_metadata":null,"created_at":"2026-07-19T02:00:03.406367Z","pmid":"38728661","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}