{"doi":"10.1002/ijch.202100015","title":"Synthesis of <i>O</i>‐linked Cyclitol Analogues of Gilvocarcin M and Antibacterial Activity","abstract":"Abstract Two unnatural regioisomeric glycosylated Gilvocarcin analogues were proposed as model compounds to study the origin behind the biosynthetic development of the Gilvocarcins, a class of bioactive C ‐aryl glycoside natural products. More specifically, the origins behind the proposed O ‐ to C ‐glycoside migration in the evolution of the biosynthesis for these classes of Angucycline antibiotic natural products. For stability reasons a 5a‐carbasugar motif was used to mimic the sugar portion of the molecule and of synthetic ease the proposed abiotic rearrangement move the sugar analogue along with its O ‐glycoside linkage. The two proposed regioisomeric analogues were synthesized by a regio‐divergent synthetic pathway and featured a Mitsunobu‐like invertive cyclictolization reaction to install the carbasugar motif. The two regioisomeric Gilvocarcin analogues were evaluated as antibiotic with Gilvocarcin M as a control. Only one of the two isomers showing weak antibiotic activity as compared to Gilvocarcin M.","journal":"Israel Journal of Chemistry","year":2021,"id":208210,"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":3,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9443,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2021-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":38215,"name":"Pei‐Yong Shi","orcid":"0000-0001-5553-1616","position":1,"is_corresponding":false},{"id":416559,"name":"George A. O’Doherty","orcid":"0000-0002-1699-2249","position":2,"is_corresponding":false},{"id":794311,"name":"Ehesan U. Sharif","orcid":"0000-0002-2605-6745","position":0,"is_corresponding":true}],"reference_count":85,"raw_metadata":null,"created_at":"2026-07-18T23:51:53.662668Z","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":[]}