{"doi":"10.1021/acs.joc.4c01674","title":"Teixobactin “Swapmers” with <scp>l</scp> Tail Stereochemistry Retain Antibiotic Activity","abstract":"High Resolution Image Download MS PowerPoint Slide The unusual d - l - l - d - d - l - l pattern of stereochemistry in residues 1–7 of the peptide antibiotic teixobactin is critical to its extraordinary antibiotic activity, creating an unusual amphiphilic β-sheetlike structure that is essential to its mechanism of action. The current study sought to replace the three d -amino acids in the tail with l -amino acids while maintaining amphiphilicity. We find that swapping residues d -Gln 4 and d - allo -Ile 5 in O -acyl isopeptide prodrugs of teixobactin permits the introduction of l -stereochemistry with retention of antibiotic activity. Nevertheless, modifying the N -terminal stereochemistry results in a loss of antibiotic activity.","journal":"The Journal of Organic Chemistry","year":2024,"id":504062,"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":0,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9511,"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":1261783,"name":"Ana-Teresa Mendoza","orcid":null,"position":1,"is_corresponding":false},{"id":168285,"name":"James S. Nowick","orcid":"0000-0002-2273-1029","position":2,"is_corresponding":false},{"id":1261283,"name":"James H. Griffin","orcid":"0009-0004-9448-1526","position":0,"is_corresponding":true}],"reference_count":16,"raw_metadata":null,"created_at":"2026-07-19T02:10:35.597333Z","pmid":"39344830","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":[]}