{"doi":"10.1073/pnas.2013691118","title":"Boronic acid with high oxidative stability and utility in biological contexts","abstract":"Significance Like thiols, boronic acids are unstable to oxidation in biological contexts, limiting their utility. We discovered that the rate-limiting step in the oxidation of a boronic acid can be slowed by the installation of a pendant carboxyl group that is a ligand to the boron atom. The ensuing boronic acid is 10,000-fold more resistant to oxidation. Experimental and computational analyses reveal that the orientational constraints and electronic effects imposed by the carboxyl group act as intended, slowing the rate-limiting step during oxidation. The new boronic acid retains the useful attributes of simple boronic acids such as forming reversible covalent bonds with saccharides and a protein and could be useful in chemical biology, medicinal chemistry, and allied fields.","journal":"Proceedings of the National Academy of Sciences","year":2021,"id":149706,"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":102,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9562,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"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":344172,"name":"Ian W. Windsor","orcid":"0000-0002-6289-6928","position":1,"is_corresponding":false},{"id":488098,"name":"Brian Gold","orcid":"0000-0002-3534-1329","position":2,"is_corresponding":false},{"id":344174,"name":"Ronald T. Raines","orcid":"0000-0001-7164-1719","position":3,"is_corresponding":false},{"id":568988,"name":"Brian J. Graham","orcid":"0000-0001-9985-3553","position":0,"is_corresponding":true}],"reference_count":73,"raw_metadata":null,"created_at":"2026-07-18T23:42:56.251607Z","pmid":"33653951","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":[]}