{"doi":"10.1002/ajoc.202100764","title":"Purine Nucleosides with a Reactive ( <i>β</i> ‐Iodovinyl)sulfone or a ( <i>β</i> ‐Keto)sulfone Group at the C8 Position and Their Polymerase‐Catalyzed Incorporation into DNA","abstract":"Abstract Iodosulfonylation of an ethynyl group attached at C8‐position of 2′‐deoxyadenosine or 2′‐deoxyguanosine A with TsNa or TsNHNH 2 , as tosyl source, and I 2 or KI, as iodide source, provided 8‐(1‐iodo‐2‐tosylvinyl) nucleosides B with ( β ‐iodovinyl)sulfone group tethered to C8 position of the purine ring. Treatment of B with ammonia followed by acid‐catalyzed hydrolysis of the intermediary β ‐sulfonylvinylamines C gave 8‐( β ‐keto)sulfones D . The iodovinylsulfone probes B undergo nucleophilic substitution of iodide with thiols or amines, via an addition‐elimination path, to provide vinyl thioethers or vinyl amines, respectively. The 8‐( β ‐keto)sulfone probes D react with electrophiles such as alkyl bromides resulting in α‐alkylation. The 5′‐triphosphate of 2′‐deoxyadenosine analog of D was incorporated by a human DNA polymerase into a double‐stranded DNA oligonucleotide possessing a one‐nucleotide gap substrate.","journal":"Asian Journal of Organic Chemistry","year":2022,"id":289783,"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":4,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.947,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2022-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":770359,"name":"Sazzad H. Suzol","orcid":"0000-0002-5515-474X","position":1,"is_corresponding":false},{"id":971849,"name":"Kevin Blanco","orcid":null,"position":2,"is_corresponding":false},{"id":971850,"name":"Lilian Martin‐Rafa","orcid":null,"position":3,"is_corresponding":false},{"id":501862,"name":"Eduardo E. Laverde","orcid":null,"position":4,"is_corresponding":false},{"id":484953,"name":"Yuan Liu","orcid":"0000-0003-4797-6396","position":5,"is_corresponding":false},{"id":545540,"name":"Stanislaw F. Wnuk","orcid":"0000-0002-3111-3919","position":6,"is_corresponding":false},{"id":770358,"name":"A. Hasan Howlader","orcid":"0000-0001-7864-2722","position":0,"is_corresponding":true}],"reference_count":55,"raw_metadata":null,"created_at":"2026-07-19T00:30:22.686776Z","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":[]}