{"created":"2021-03-01T06:31:43.972372+00:00","id":23847,"links":{},"metadata":{"_buckets":{"deposit":"c73efb25-4d12-469b-84e2-dd718af45aab"},"_deposit":{"id":"23847","owners":[],"pid":{"revision_id":0,"type":"depid","value":"23847"},"status":"published"},"_oai":{"id":"oai:nagoya.repo.nii.ac.jp:00023847","sets":["1903:1904:1905"]},"author_link":["70768","70769","70770","70771","70772","70773"],"item_10_biblio_info_6":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2016-12-13","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"1","bibliographicPageEnd":"36","bibliographicPageStart":"25","bibliographicVolumeNumber":"82","bibliographic_titles":[{"bibliographic_title":"Journal of Organic Chemistry","bibliographic_titleLang":"en"}]}]},"item_10_description_4":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"Conformationally restricted nucleoside analogues 2′,4′-BNA/LNA-7-deazaguanine (LNA-7cG) and 2′,4′-BNA/LNA-8-aza-7-deazaguanine (LNA-8n7cG), which avoid extra hydrogen bond formation at the 7-position of the guanine nucleobase, were successfully synthesized and incorporated into oligonucleotides. While the LNA-7cG-containing oligonucleotides show high duplex-forming ability with complementary DNA and RNA similar to LNA-G, the LNA-8n7cG-containing oligonucleotide has lower binding affinity than that of natural 2′-deoxyguanosine. This disparity in thermostability is also observed in 7-deazaadenosine analogues (LNA-7cA, LNA-8n7cA). Thermodynamic parameters and computational chemistry revealed that an inappropriate glycosidic torsion angle χ of 2′,4′-BNA/LNA-8-aza-7-deazapurine analogues destabilizes duplex formation in contrast to 2′,4′-BNA/LNA-7-deazapurine analogues. This result indicates that the nucleobase rotation angle plays an important role in duplex binding affinity. In addition, LNA-7cG-modified oligonucleotide effectively suppresses aggregation even in a guanine-rich sequence.","subitem_description_language":"en","subitem_description_type":"Abstract"}]},"item_10_identifier_60":{"attribute_name":"URI","attribute_value_mlt":[{"subitem_identifier_type":"DOI","subitem_identifier_uri":"http://doi.org/10.1021/acs.joc.6b02525"},{"subitem_identifier_type":"HDL","subitem_identifier_uri":"http://hdl.handle.net/2237/26026"}]},"item_10_publisher_32":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"ACS Publications","subitem_publisher_language":"en"}]},"item_10_relation_11":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_type":"isVersionOf","subitem_relation_type_id":{"subitem_relation_type_id_text":"https://doi.org/10.1021/acs.joc.6b02525","subitem_relation_type_select":"DOI"}}]},"item_10_rights_12":{"attribute_name":"権利","attribute_value_mlt":[{"subitem_rights":"“This document is the Accepted Manuscript version of a Published Work that appeared in final form in [Journal of Organic Chemistry], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [<br/>http://pubs.acs.org/articlesonrequest/AOR-ydEFrgSbiWvtaGvc398M].”","subitem_rights_language":"en"}]},"item_10_select_15":{"attribute_name":"著者版フラグ","attribute_value_mlt":[{"subitem_select_item":"author"}]},"item_10_source_id_7":{"attribute_name":"ISSN","attribute_value_mlt":[{"subitem_source_identifier":"0022-3263","subitem_source_identifier_type":"PISSN"}]},"item_1615787544753":{"attribute_name":"出版タイプ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_ab4af688f83e57aa","subitem_version_type":"AM"}]},"item_access_right":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"open access","subitem_access_right_uri":"http://purl.org/coar/access_right/c_abf2"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Hara, Takashi","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"70768","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Kodama, Tetsuya","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"70769","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Takegaki, Yumi","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"70770","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Morihiro, Kunihiko","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"70771","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ito, Ramon　Kosuke","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"70772","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Obika, Satoshi","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"70773","nameIdentifierScheme":"WEKO"}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2017-12-13"}],"displaytype":"detail","filename":"jo-2016-02525x_Revised_manuscript.pdf","filesize":[{"value":"8.0 MB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"jo-2016-02525x_Revised_manuscript.pdf ファイル公開：2017/12/13","objectType":"fulltext","url":"https://nagoya.repo.nii.ac.jp/record/23847/files/jo-2016-02525x_Revised_manuscript.pdf"},"version_id":"531f05c9-3e83-48e1-b873-707b226a9366"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"Synthesis and Properties of 7-Deazapurine- and 8-Aza-7-deazapurine-Locked Nucleic Acid Analogues: Effect of the Glycosidic Torsion Angle","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Synthesis and Properties of 7-Deazapurine- and 8-Aza-7-deazapurine-Locked Nucleic Acid Analogues: Effect of the Glycosidic Torsion Angle","subitem_title_language":"en"}]},"item_type_id":"10","owner":"1","path":["1905"],"pubdate":{"attribute_name":"PubDate","attribute_value":"2017-04-18"},"publish_date":"2017-04-18","publish_status":"0","recid":"23847","relation_version_is_last":true,"title":["Synthesis and Properties of 7-Deazapurine- and 8-Aza-7-deazapurine-Locked Nucleic Acid Analogues: Effect of the Glycosidic Torsion Angle"],"weko_creator_id":"1","weko_shared_id":-1},"updated":"2023-01-16T05:03:43.041857+00:00"}