{"doi":"10.1002/cbic.201900015","title":"Genetically Encoded Biotin Analogues: Incorporation and Application in Bacterial and Mammalian Cells","abstract":"<jats:title>Abstract</jats:title><jats:p>The biotin–streptavidin interaction is among the strongest known in nature. Herein, the site‐directed incorporation of biotin and 2‐iminobiotin composed of noncanonical amino acids (ncAAs) into proteins is reported. 2‐Iminobiotin lysine was employed for protein purification based on the pH‐dependent dissociation constant to streptavidin. By using the high‐affinity binding of biotin lysine, the bacterial protein RecA could be specifically isolated and its interaction partners analyzed. Furthermore, the biotinylation approach was successfully transferred to mammalian cells. Stringent control over the biotinylation site and the tunable affinity between ncAAs and streptavidin of the different biotin analogues make this approach an attractive tool for protein interaction studies, protein immobilization, and the generation of well‐defined protein–drug conjugates.</jats:p>","journal":"ChemBioChem","year":2019,"id":14738,"datarank":0.24748929618083015,"base_score":1.3862943611198906,"endowment":1.3862943611198906,"self_citation_contribution":0.20794415416798362,"citation_network_contribution":0.03954514201284653,"self_endowment_contribution":0.20794415416798362,"citer_contribution":0.03954514201284653,"corpus_percentile":null,"corpus_rank":null,"citation_count":3,"citer_count":3,"citers_with_citation_signal":3,"citers_with_endowment":3,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":115160,"name":"Yonatan G. 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Feige","orcid":null,"position":8,"is_corresponding":false},{"id":115168,"name":"Jörg Eppinger","orcid":null,"position":9,"is_corresponding":false},{"id":115159,"name":"Adrian Hohl","orcid":"0000-0001-5167-9912","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":1.3862943611198906,"endowment":1.3862943611198906,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"30900320","pmcid":null,"openalex_id":"https://openalex.org/W2923238538","authors":[],"funders":[{"funder_name":"King Abdullah University of Science and Technology","grant_id":"Fund","title":null},{"funder_name":"Deutsche Forschungsgemeinschaft","grant_id":"1035","title":null},{"funder_name":"Deutsche Forschungsgemeinschaft","grant_id":"unidentified","title":"unidentified"}],"total_grants":3,"fwci":0.1133,"citation_percentile":0.44110922,"influential_citations":0,"citation_trend":[{"year":2022,"count":1},{"year":2024,"count":1},{"year":2025,"count":1}],"oa_status":"closed","license":"Wiley Online Library User Agreement","oa_locations":[{"url":"https://repository.kaust.edu.sa/bitstreams/e4830984-9cc9-4ed1-980e-dfc823392214/download","host_type":"GREEN"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/cbic.201900015","host_type":"publisher"},{"url":"https://chemistry-europe.onlinelibrary.wiley.com/doi/pdf/10.1002/cbic.201900015","host_type":"publisher"},{"url":"https://doi.org/10.1002/cbic.201900015","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/30900320","host_type":"repository"},{"url":"http://hdl.handle.net/10754/631758","host_type":"repository"},{"url":"https://repository.kaust.edu.sa/bitstream/10754/631758/1/Hohl_et_al-2019-ChemBioChem.pdf","host_type":""},{"url":"https://dx.doi.org/10.1002/cbic.201900015","host_type":""},{"url":"https://doi.org/https://doi.org/10.1002/cbic.201900015","host_type":""}],"fields_of_study":["Biotin and Related Studies","Click Chemistry and Applications","Peptidase Inhibition and Analysis","Political Science","Medicine","Biology","Chemistry","0301 basic medicine","0303 health sciences","03 medical and health sciences","Amino Acyl-tRNA Synthetases","Archaeal Proteins","Biotin","Biotinylation","Escherichia coli","HEK293 Cells","Humans","Lysine","Methanosarcina barkeri","Mutation","Protein Binding","Protein Processing, Post-Translational","Rec A Recombinases","Streptavidin"],"mesh_terms":["Amino Acyl-tRNA Synthetases","Biotin","Escherichia coli","Humans","Lysine","Mutation","Protein Binding","Protein Processing, Post-Translational","Rec A Recombinases","Methanosarcina barkeri","Streptavidin","Archaeal Proteins","Biotinylation","HEK293 Cells"],"keywords":["Biotinylation","Biotin","Streptavidin","Biochemistry","Lysine","Chemistry","Amino acid","Protein engineering","Enzyme","Proteins","Amino acids","Mutagenesis","Noncovalent Interactions","Archaeal Proteins","amber suppression","Amino Acyl-tRNA Synthetases","biotinylated amino acid","Rec A Recombinases","HEK293 Cells","Mutation","Escherichia coli","Humans","pyrrolysyl-tRNA synthetase","Methanosarcina barkeri","site-specific incorporation","Protein Processing, Post-Translational","unnatural amino acids","Protein Binding"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-01T14:09:08.843402Z","pmid":null,"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":[]}