{"doi":"10.1002/chem.202403767","title":"Total Synthesis and Structural Reassignment of the Antitubercular Natural Product Evybactin","abstract":"The escalating threat posed by antibiotic resistance is a global concern and underscores the need for new antibiotics. In this context, the recent discovery of evybactin, a nonribosomal depsipeptide antibiotic that selectively and potently inhibits the growth of M. tuberculosis, is particularly noteworthy. Here, we present the first total synthesis of this natural product, along with a revision of its assigned structure. Our studies revealed a disparity between the structure originally proposed for evybactin and its actual configuration. Specifically, the 3-methylhistidine residue present in the evybactin core macrocycle was found to be of the d-configuration rather than the previously assigned l-His(Me). Having addressed this, we further optimized our solid-phase synthetic route to provide access to evybactin on a multi-hundred-milligram scale. Access to such quantities will allow for more comprehensive studies with this promising antibiotic.","journal":"Chemistry - A European Journal","year":2024,"id":449396,"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":5,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9435,"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":655419,"name":"Sangkeun Son","orcid":"0000-0002-4574-288X","position":1,"is_corresponding":false},{"id":623624,"name":"Monique Theriault","orcid":"0000-0002-9502-3402","position":2,"is_corresponding":false},{"id":1268728,"name":"Cornelis J. Slingerland","orcid":"0000-0003-0027-7491","position":3,"is_corresponding":false},{"id":1268729,"name":"Glenn Hauk","orcid":"0000-0003-4325-7335","position":4,"is_corresponding":false},{"id":1268730,"name":"Laurence Cleenewerk","orcid":"0000-0003-3538-0288","position":5,"is_corresponding":false},{"id":1268731,"name":"Alexander Speer","orcid":"0000-0001-7142-5987","position":6,"is_corresponding":false},{"id":62557,"name":"James M. Berger","orcid":"0000-0003-0666-1240","position":7,"is_corresponding":false},{"id":108493,"name":"Kim Lewis","orcid":"0000-0002-1335-9982","position":8,"is_corresponding":false},{"id":1014145,"name":"Nathaniel I. Martin","orcid":"0000-0001-8246-3006","position":9,"is_corresponding":false},{"id":1268727,"name":"Vladyslav Lysenko","orcid":"0000-0001-9236-5821","position":0,"is_corresponding":true}],"reference_count":24,"raw_metadata":null,"created_at":"2026-07-19T02:02:16.291892Z","pmid":"39412482","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":[]}