{"doi":"10.1002/anie.202000523","title":"Total Synthesis of a Mycolic Acid from <i>Mycobacterium tuberculosis</i>","abstract":"In Mycobacterium tuberculosis, mycolic acids and their glycerol, glucose, and trehalose esters (\"cord factor\") form the main part of the mycomembrane. Despite their first isolation almost a century ago, full stereochemical evaluation is lacking, as is a scalable synthesis required for accurate immunological, including vaccination, studies. Herein, we report an efficient, convergent, gram-scale synthesis of four stereo-isomers of a mycolic acid and its glucose ester. Binding to the antigen presenting protein CD1b and T cell activation studies are used to confirm the antigenicity of the synthetic material. The absolute stereochemistry of the syn-methoxy methyl moiety in natural material is evaluated by comparing its optical rotation with that of synthetic material.","journal":"Angewandte Chemie International Edition","year":2020,"id":100525,"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":28,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9491,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2020-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":493560,"name":"Peter Fodran","orcid":"0000-0003-0348-8331","position":1,"is_corresponding":false},{"id":494627,"name":"Jayaraman Dhineshkumar","orcid":null,"position":2,"is_corresponding":false},{"id":493561,"name":"Jeffrey Buter","orcid":"0000-0002-4440-6702","position":3,"is_corresponding":false},{"id":493562,"name":"Martin D. Witte","orcid":"0000-0003-4660-2974","position":4,"is_corresponding":false},{"id":312630,"name":"Tonatiuh A. Ocampo","orcid":"0000-0001-5443-9519","position":5,"is_corresponding":false},{"id":312635,"name":"D. Branch Moody","orcid":"0000-0003-2306-3058","position":6,"is_corresponding":false},{"id":252300,"name":"Ildiko Van Rhijn","orcid":"0000-0002-1446-5701","position":7,"is_corresponding":false},{"id":493563,"name":"Adriaan J. Minnaard","orcid":"0000-0002-5966-1300","position":8,"is_corresponding":false},{"id":494626,"name":"Nabil Tahiri","orcid":null,"position":0,"is_corresponding":true}],"reference_count":31,"raw_metadata":null,"created_at":"2026-07-18T22:39:01.863288Z","pmid":"32067294","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":[]}