{"doi":"10.1016/j.bmc.2004.02.039","title":"An o-nitrobenzyl scaffold for peptide ligation: synthesis and applications","abstract":null,"journal":"Bioorganic & Medicinal Chemistry","year":2004,"id":689148,"datarank":0.6716005221717312,"base_score":4.477336814478207,"endowment":4.477336814478207,"self_citation_contribution":0.6716005221717312,"citation_network_contribution":0.0,"self_endowment_contribution":0.6716005221717312,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":87,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1759944,"name":"John Offer","orcid":null,"position":1,"is_corresponding":false},{"id":1739137,"name":"Renato Longhi","orcid":null,"position":2,"is_corresponding":false},{"id":342712,"name":"Philip E. Dawson","orcid":"0000-0002-2538-603X","position":3,"is_corresponding":false},{"id":1800363,"name":"Chiara Marinzi","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"An o-nitrobenzyl scaffold for peptide ligation: synthesis and applications","abstract":"Chemical ligation approaches facilitate the chemoselective assembly of unprotected peptides in aqueous solution. Here, two photolabile auxiliaries are described that enlarge the applicability of native chemical ligation to non-cysteine targets. The auxiliaries, designed to allow reaction with thioester peptides, generate an amide bond between the two initial fragments. The o-nitrobenzyl tertiary benzylamide that is formed at the ligation junction can be transformed into a native amide group under mild photolysis conditions. The veratryl auxiliary was found to be excessively labile during peptide purification and ligation. However, the auxiliary based on the o-nitrobenzyl group shows all the necessary properties for a general application in routine peptide and protein synthesis. In addition, the auxiliary linked to the N-terminus can be efficiently photolyzed, suggesting a new approach for the generation of photocaged amines. Synthesis, solid phase introduction onto peptide chains, ligation properties and photolysis in water are described, and a careful study of compatibility of the method with potentially fragile peptide side chains is reported.","is_dataset_classified":null,"base_score":4.477336814478207,"endowment":4.477336814478207,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"15110856","pmcid":null,"openalex_id":"https://openalex.org/W2046621823","authors":[],"funders":[{"funder_name":"NIMH NIH HHS","grant_id":"MH62261","title":null}],"total_grants":1,"fwci":1.4759,"citation_percentile":0.80080083,"influential_citations":0,"citation_trend":[{"year":2012,"count":4},{"year":2013,"count":3},{"year":2014,"count":4},{"year":2015,"count":9},{"year":2016,"count":2},{"year":2017,"count":2},{"year":2018,"count":1},{"year":2019,"count":3},{"year":2020,"count":4},{"year":2021,"count":4},{"year":2022,"count":1},{"year":2023,"count":3},{"year":2024,"count":2}],"oa_status":"closed","license":"https://www.elsevier.com/legal/tdmrep-license","oa_locations":[{"url":"https://api.elsevier.com/content/article/PII:S0968089604001658?httpAccept=text/xml","host_type":"publisher"},{"url":"https://api.elsevier.com/content/article/PII:S0968089604001658?httpAccept=text/plain","host_type":"publisher"},{"url":"https://doi.org/10.1016/j.bmc.2004.02.039","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/15110856","host_type":"repository"}],"fields_of_study":["Chemical Synthesis and Analysis","Click Chemistry and Applications","Antimicrobial Peptides and Activities","Nitrobenzenes","Peptides","Photolysis","Solutions"],"mesh_terms":["Nitrobenzenes","Peptides","Photolysis","Solutions"],"keywords":["Native chemical ligation","Chemistry","Chemical ligation","Peptide","Ligation","Thioester","Combinatorial chemistry","Amide","Peptide synthesis","Peptide bond","Cysteine","Solid-phase synthesis","Chemical synthesis","Organic chemistry","Biochemistry","In vitro"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Clean water and sanitation"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-19T23:03:42.730778Z","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":[]}