{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,11]],"date-time":"2026-02-11T13:23:33Z","timestamp":1770816213873,"version":"3.50.1"},"reference-count":13,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2025,3,27]],"date-time":"2025-03-27T00:00:00Z","timestamp":1743033600000},"content-version":"vor","delay-in-days":26,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Current Protocols"],"published-print":{"date-parts":[[2025,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Boranophosphate DNAs, in which one of the nonbridging oxygen atoms in the phosphate moiety is replaced with a borano group, are promising antisense oligonucleotide candidates because of their high nuclease resistance and low cytotoxicity. In Basic Protocol 1, we describe the synthesis of a dithymidylate boranophosphodiester via a boranophosphotriester method. Using the boranophosphotriester method, the condensation of a deoxyribonucleoside 3\u2019\u2010<jats:italic>O<\/jats:italic>\u2010boranophosphodiester, which contains a borano group with a 5\u2019\u2010hydroxy group of another deoxyribonucleoside, followed by the deprotection of a protecting group at the phosphorus center, is conducted to yield a boranophosphodiester. A boranophosphodiester is also a useful synthetic precursor, and several <jats:italic>P<\/jats:italic>\u2010modified nucleic acid derivatives can be successfully synthesized via the conversion reaction of a boranophosphodiester. In Basic Protocol 2, we describe the conversion reaction of the boranophosphodiester through an acyl phosphite intermediate. During the conversion reaction, various <jats:italic>P<\/jats:italic>\u2010modified nucleic acid derivatives, such as a phosphorothioate diester, phosphotriester, phosphoramidate, phosphorothioate triester, and phosphorothioamidate, are obtained in good yields (69% to 93%). \u00a9 2025 Wiley Periodicals LLC.<\/jats:p><jats:p><jats:bold>Basic Protocol 1<\/jats:bold>: Synthesis of dithymidylate boranophosphodiester<\/jats:p><jats:p><jats:bold>Support Protocol 1<\/jats:bold>: Preparation of 3\u2010[(trimethylsilyl)oxy]propanenitrile<\/jats:p><jats:p><jats:bold>Support Protocol 2<\/jats:bold>: Preparation of PyNTP<\/jats:p><jats:p><jats:bold>Support Protocol 3<\/jats:bold>: Preparation of compound <jats:bold>7<\/jats:bold><\/jats:p><jats:p><jats:bold>Basic Protocol 2<\/jats:bold>: One\u2010pot synthesis of <jats:italic>P<\/jats:italic>\u2010modified nucleic acid derivatives<\/jats:p>","DOI":"10.1002\/cpz1.70117","type":"journal-article","created":{"date-parts":[[2025,3,27]],"date-time":"2025-03-27T09:51:18Z","timestamp":1743069078000},"source":"Crossref","is-referenced-by-count":1,"title":["Preparation of Boranophosphate DNA via the Boranophosphotriester Method and Synthesis of <i>P<\/i>\u2010modified DNAs from Boranophosphate DNA via an Acyl Phosphite Intermediate"],"prefix":"10.1002","volume":"5","author":[{"given":"Yuhei","family":"Takahashi","sequence":"first","affiliation":[{"name":"Department of Medicinal and Life Sciences, Faculty of Pharmaceutical Sciences Tokyo University of Science  Noda Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kazuki","family":"Sato","sequence":"additional","affiliation":[{"name":"Department of Medicinal and Life Sciences, Faculty of Pharmaceutical Sciences Tokyo University of Science  Noda Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7403-4033","authenticated-orcid":false,"given":"Takeshi","family":"Wada","sequence":"additional","affiliation":[{"name":"Department of Medicinal and Life Sciences, Faculty of Pharmaceutical Sciences Tokyo University of Science  Noda Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,3,27]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104020(01)88752\u20104"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/c4ob02258k"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr050009p"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201801479"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cpnc.82"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.01.084"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/c6ob02309f"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0603779"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo0493875"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar010049p"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c00659"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo500185b"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol801608j"}],"container-title":["Current Protocols"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cpz1.70117","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,2]],"date-time":"2025-05-02T13:09:41Z","timestamp":1746191381000},"score":1,"resource":{"primary":{"URL":"https:\/\/currentprotocols.onlinelibrary.wiley.com\/doi\/10.1002\/cpz1.70117"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3]]},"references-count":13,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2025,3]]}},"alternative-id":["10.1002\/cpz1.70117"],"URL":"https:\/\/doi.org\/10.1002\/cpz1.70117","archive":["Portico"],"relation":{},"ISSN":["2691-1299","2691-1299"],"issn-type":[{"value":"2691-1299","type":"print"},{"value":"2691-1299","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,3]]},"article-number":"e70117"}}