{"external_id":{"isi":["000866428500001"]},"publication_identifier":{"issn":["1433-7851"],"eissn":["1521-3773"]},"doi":"10.1002/anie.202211945","publication":"Angewandte Chemie International Edition","author":[{"first_name":"Felix","last_name":"Xu","full_name":"Xu, Felix"},{"full_name":"Crisp, Antony","first_name":"Antony","last_name":"Crisp"},{"last_name":"Schinkel","first_name":"Thea","full_name":"Schinkel, Thea"},{"full_name":"Dubini, Romeo C. A.","first_name":"Romeo C. A.","last_name":"Dubini"},{"first_name":"Sarah","last_name":"Hübner","full_name":"Hübner, Sarah"},{"first_name":"Sidney","last_name":"Becker","full_name":"Becker, Sidney"},{"full_name":"Schelter, Florian","first_name":"Florian","last_name":"Schelter"},{"last_name":"Rovo","first_name":"Petra","full_name":"Rovo, Petra","id":"c316e53f-b965-11eb-b128-bb26acc59c00","orcid":"0000-0001-8729-7326"},{"last_name":"Carell","first_name":"Thomas","full_name":"Carell, Thomas"}],"has_accepted_license":"1","language":[{"iso":"eng"}],"article_number":"e202211945","_id":"12228","citation":{"mla":"Xu, Felix, et al. “Isoxazole Nucleosides as Building Blocks for a Plausible Proto‐RNA.” <i>Angewandte Chemie International Edition</i>, vol. 61, no. 45, e202211945, Wiley, 2022, doi:<a href=\"https://doi.org/10.1002/anie.202211945\">10.1002/anie.202211945</a>.","ieee":"F. Xu <i>et al.</i>, “Isoxazole nucleosides as building blocks for a plausible proto‐RNA,” <i>Angewandte Chemie International Edition</i>, vol. 61, no. 45. Wiley, 2022.","chicago":"Xu, Felix, Antony Crisp, Thea Schinkel, Romeo C. A. Dubini, Sarah Hübner, Sidney Becker, Florian Schelter, Petra Rovo, and Thomas Carell. “Isoxazole Nucleosides as Building Blocks for a Plausible Proto‐RNA.” <i>Angewandte Chemie International Edition</i>. Wiley, 2022. <a href=\"https://doi.org/10.1002/anie.202211945\">https://doi.org/10.1002/anie.202211945</a>.","ista":"Xu F, Crisp A, Schinkel T, Dubini RCA, Hübner S, Becker S, Schelter F, Rovo P, Carell T. 2022. Isoxazole nucleosides as building blocks for a plausible proto‐RNA. Angewandte Chemie International Edition. 61(45), e202211945.","apa":"Xu, F., Crisp, A., Schinkel, T., Dubini, R. C. A., Hübner, S., Becker, S., … Carell, T. (2022). Isoxazole nucleosides as building blocks for a plausible proto‐RNA. <i>Angewandte Chemie International Edition</i>. Wiley. <a href=\"https://doi.org/10.1002/anie.202211945\">https://doi.org/10.1002/anie.202211945</a>","ama":"Xu F, Crisp A, Schinkel T, et al. Isoxazole nucleosides as building blocks for a plausible proto‐RNA. <i>Angewandte Chemie International Edition</i>. 2022;61(45). doi:<a href=\"https://doi.org/10.1002/anie.202211945\">10.1002/anie.202211945</a>","short":"F. Xu, A. Crisp, T. Schinkel, R.C.A. Dubini, S. Hübner, S. Becker, F. Schelter, P. Rovo, T. Carell, Angewandte Chemie International Edition 61 (2022)."},"article_type":"original","year":"2022","intvolume":"        61","volume":61,"ddc":["540"],"keyword":["General Chemistry","Catalysis"],"isi":1,"acknowledgement":"We thank Stefan Wiedemann for the synthesis of reference compounds and Pia Heinrichs for assistance in the NMR measurements of the oligonucleotides. We also thank Dr. Luis Escobar and Jonas Feldmann for valued discussions. This work was supported by the German Research Foundation (DFG) for financial support via CRC1309 (Project ID 325871075, A04), CRC1361 (Project ID 893547839, P02) and CRC1032 (Project ID 201269156, A5). This project has received funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program under grant agreement No 741912 (EpiR). We are grateful for additional funding from the Volkswagen Foundation (EvoRib). Open Access funding enabled and organized by Projekt DEAL.","file_date_updated":"2023-01-27T10:28:45Z","article_processing_charge":"No","month":"11","tmp":{"image":"/images/cc_by.png","name":"Creative Commons Attribution 4.0 International Public License (CC-BY 4.0)","short":"CC BY (4.0)","legal_code_url":"https://creativecommons.org/licenses/by/4.0/legalcode"},"date_updated":"2023-08-04T09:32:42Z","file":[{"date_created":"2023-01-27T10:28:45Z","file_size":1076715,"success":1,"file_id":"12422","date_updated":"2023-01-27T10:28:45Z","access_level":"open_access","creator":"dernst","file_name":"2022_AngewandteChemieInternat_Xu.pdf","content_type":"application/pdf","checksum":"4e8152454d12025d13f6e6e9ca06b5d0","relation":"main_file"}],"type":"journal_article","day":"07","department":[{"_id":"NMR"}],"abstract":[{"lang":"eng","text":"The question of how RNA, as the principal carrier of genetic information evolved is fundamentally important for our understanding of the origin of life. The RNA molecule is far too complex to have formed in one evolutionary step, suggesting that ancestral proto-RNAs (first ancestor of RNA) may have existed, which evolved over time into the RNA of today. Here we show that isoxazole nucleosides, which are quickly formed from hydroxylamine, cyanoacetylene, urea and ribose, are plausible precursors for RNA. The isoxazole nucleoside can rearrange within an RNA-strand to give cytidine, which leads to an increase of pairing stability. If the proto-RNA contains a canonical seed-nucleoside with defined stereochemistry, the seed-nucleoside can control the configuration of the anomeric center that forms during the in-RNA transformation. The results demonstrate that RNA could have emerged from evolutionarily primitive precursor isoxazole ribosides after strand formation."}],"date_published":"2022-11-07T00:00:00Z","publication_status":"published","issue":"45","publisher":"Wiley","scopus_import":"1","oa":1,"oa_version":"Published Version","date_created":"2023-01-16T09:49:05Z","user_id":"4359f0d1-fa6c-11eb-b949-802e58b17ae8","quality_controlled":"1","title":"Isoxazole nucleosides as building blocks for a plausible proto‐RNA","status":"public"}