{"doi":"10.1021/jo011148j","title":"Peptidotriazoles on Solid Phase:  [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides","abstract":"The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely 1,4-substituted [1,2,3]-triazoles in peptide backbones or side chains. The reaction conditions were fully compatible with solid-phase peptide synthesis on polar supports. The copper(I) catalysis is mild and efficient (>95% conversion and purity in most cases) and furthermore, the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1,3-dipoles entering the reaction. Novel Fmoc-protected amino azides derived from Fmoc-amino alcohols were prepared by the Mitsunobu reaction.","journal":"The Journal of Organic Chemistry","year":2002,"id":9912,"datarank":19.68011614847148,"base_score":9.040263541598666,"endowment":9.040263541598666,"self_citation_contribution":1.3560395312398001,"citation_network_contribution":18.32407661723168,"self_endowment_contribution":1.3560395312398001,"citer_contribution":18.32407661723168,"corpus_percentile":94.7,"corpus_rank":1115,"citation_count":8435,"citer_count":198,"citers_with_citation_signal":198,"citers_with_endowment":198,"datacite_reuse_total":0,"is_dataset":false,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2002-04-02","authors":[{"id":84965,"name":"Caspar Christensen","orcid":"0000-0002-0214-8477","position":1,"is_corresponding":false},{"id":84966,"name":"Morten Meldal","orcid":"0000-0001-6114-9018","position":2,"is_corresponding":false},{"id":84964,"name":"Christian W. Tornøe","orcid":"0000-0002-6549-1213","position":0,"is_corresponding":true}],"reference_count":29,"raw_metadata":{"citation_network_status":"fetched"},"created_at":"2026-03-01T18:20:47.508186Z","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,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}