{"doi":"10.1002/anie.202005300","title":"Independent Generation and Time‐Resolved Detection of 2′‐Deoxyguanosin‐<i>N2</i>‐yl Radicals","abstract":"Abstract Guanine radicals are important reactive intermediates in DNA damage. Hydroxyl radical (HO . ) has long been believed to react with 2′‐deoxyguanosine (dG) generating 2′‐deoxyguanosin‐N1‐yl radical (dG(N1‐H) . ) via addition to the nucleobase π‐system and subsequent dehydration. This basic tenet was challenged by an alternative mechanism, in which the major reaction of HO . with dG was proposed to involve hydrogen atom abstraction from the N2‐amine. The 2′‐deoxyguanosin‐N2‐yl radical (dG(N2‐H) . ) formed was proposed to rapidly tautomerize to dG(N1‐H) . . We report the first independent generation of dG(N2‐H) . in high yield via photolysis of 1 . dG(N2‐H) . is directly observed upon nanosecond laser flash photolysis (LFP) of 1 . The absorption spectrum of dG(N2‐H) . is corroborated by DFT studies, and anti ‐ and syn ‐dG(N2‐H) . are resolved for the first time. The LFP experiments showed no evidence for tautomerization of dG(N2‐H) . to dG(N1‐H) . within hundreds of microseconds. This observation suggests that the generation of dG(N1‐H) . via dG(N2‐H) . following hydrogen atom abstraction from dG is unlikely to be a major pathway when HO . reacts with dG.","journal":"Angewandte Chemie International Edition","year":2020,"id":73975,"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":12,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9621,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2020-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":389244,"name":"Xiaojuan Dai","orcid":null,"position":1,"is_corresponding":false},{"id":346008,"name":"Hongmei Su","orcid":"0000-0001-7384-6523","position":2,"is_corresponding":false},{"id":387543,"name":"Marc M. Greenberg","orcid":"0000-0002-5786-6118","position":3,"is_corresponding":false},{"id":387538,"name":"Liwei Zheng","orcid":"0000-0002-1611-2213","position":0,"is_corresponding":true}],"reference_count":43,"raw_metadata":null,"created_at":"2026-07-18T21:45:52.171053Z","pmid":"32365264","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":[]}