{"doi":"10.1002/chem.202500713","title":"Mediated Electrochemical Oxidation of Nucleosides to Their 5′‐Carboxylic Acid Derivatives","abstract":"Nucleoside 5'-carboxylic acids are important synthetic targets, but most existing methods to access these compounds use (super)stoichiometric chemical oxidants to oxidize the primary alcohol. The present study introduces an aminoxyl-mediated electrochemical method for oxidation of nucleosides and ribosugars to afford their 5'-carboxylic acid derivatives. The optimized conditions employ 4-acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (ACT) as the aminoxyl mediator in a water/acetonitrile solvent mixture with tetraethylammonium bicarbonate or monohydrogen phosphate as a base within an undivided electrolysis cell. The reaction tolerates diverse functionality at the nucleobase and sugar positions and is showcased in the oxidation of 10 different substrates, including a 10 g scale oxidation of 2'-O-methylcytidine.","journal":"Chemistry - A European Journal","year":2025,"id":552092,"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":1,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9475,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2025-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":488190,"name":"Mathew R. Johnson","orcid":"0000-0001-7456-6304","position":1,"is_corresponding":false},{"id":652220,"name":"Caitlin R. Lacker","orcid":"0000-0003-2531-2636","position":2,"is_corresponding":false},{"id":300706,"name":"Tehshik P. Yoon","orcid":"0000-0002-3934-4973","position":3,"is_corresponding":false},{"id":1207817,"name":"Joseph R. Martinelli","orcid":null,"position":4,"is_corresponding":false},{"id":110277,"name":"Shannon S. Stahl","orcid":"0000-0002-9000-7665","position":5,"is_corresponding":false},{"id":1016570,"name":"Dylan J. Abrams","orcid":"0000-0001-8514-3972","position":0,"is_corresponding":true}],"reference_count":42,"raw_metadata":null,"created_at":"2026-07-19T02:54:29.318076Z","pmid":"40114464","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":[]}