{"created":"2024-09-25T02:45:47.097200+00:00","id":2000210,"links":{},"metadata":{"_buckets":{"deposit":"32fefcea-5442-41ea-b485-16e7a87a4d6f"},"_deposit":{"created_by":51,"id":"2000210","owner":"51","owners":[51],"pid":{"revision_id":0,"type":"depid","value":"2000210"},"status":"published"},"_oai":{"id":"oai:tokushima-u.repo.nii.ac.jp:02000210","sets":["1713853213384:1713853295607"]},"author_link":["378","829","736"],"control_number":"2000210","item_10001_biblio_info_7":{"attribute_name":"bibliographic_information","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2023-04-06","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"7","bibliographicPageStart":"3265","bibliographicVolumeNumber":"28","bibliographic_titles":[{"bibliographic_title":"Molecules","bibliographic_titleLang":"en"}]}]},"item_10001_description_5":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"5-Amino-1-β-D-ribofuranosylimidazole-4-carboxamide 5′-monophosphate (ZMP) is a central intermediate in de novo purine nucleotide biosynthesis. Its nucleobase moiety, 5-aminoimidazole-4-carboxamide (Z-base), is considered an ambiguous base that can pair with any canonical base owing to the rotatable nature of its 5-carboxamide group. This idea of ambiguous base pairing due to free rotation of the carboxamide has been applied to designing mutagenic antiviral nucleosides, such as ribavirin and T-705. However, the ambiguous base-pairing ability of Z-base has not been elucidated, because the synthesis of Z-base-containing oligomers is problematic. Herein, we propose a practical method for the synthesis of Z-base-containing DNA oligomers based on the ring-opening reaction of an N1-dinitrophenylhypoxanthine (HxaDNP) base. Thermal denaturation studies of the resulting oligomers revealed that the Z-base behaves physiologically as an A-like nucleobase, preferentially forming pairs with T. We tested the behavior of Z-base-containing DNA oligomers in enzyme-catalyzed reactions: in single nucleotide insertion, Klenow fragment DNA polymerase recognized Z-base as an A-like analog and incorporated dTTP as a complementary nucleotide to Z-base in the DNA template; in PCR amplification, Taq DNA polymerase similarly incorporated dTTP as a complementary nucleotide to Z-base. Our findings will contribute to the development of new mutagenic antiviral nucleoside analogs.","subitem_description_language":"en","subitem_description_type":"Abstract"}]},"item_10001_publisher_8":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"MDPI","subitem_publisher_language":"en"}]},"item_10001_rights_15":{"attribute_name":"item_10001_rights_15","attribute_value_mlt":[{"subitem_rights":"This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.","subitem_rights_language":"en"}]},"item_10001_source_id_9":{"attribute_name":"収録物ID","attribute_value_mlt":[{"subitem_source_identifier":"14203049","subitem_source_identifier_type":"EISSN"}]},"item_10001_version_type_20":{"attribute_name":"出版タイプ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_970fb48d4fbd8a85","subitem_version_type":"VoR"}]},"item_1715043197608":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"open 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oligonucleotide","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"5-aminoimidazole-4-carboxamide","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"single nucleotide insertion","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"base-pairing property","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"melting temperature","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"mutagenic nucleosides","subitem_subject_language":"en","subitem_subject_scheme":"Other"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"item_resource_type","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"Synthesis and Behavior of DNA Oligomers Containing the Ambiguous Z-Nucleobase 5-Aminoimidazole-4-carboxamide","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Synthesis and Behavior of DNA Oligomers Containing the Ambiguous Z-Nucleobase 5-Aminoimidazole-4-carboxamide","subitem_title_language":"en"}]},"item_type_id":"40001","owner":"51","path":["1713853295607"],"pubdate":{"attribute_name":"PubDate","attribute_value":"2024-10-22"},"publish_date":"2024-10-22","publish_status":"0","recid":"2000210","relation_version_is_last":true,"title":["Synthesis and Behavior of DNA Oligomers Containing the Ambiguous Z-Nucleobase 5-Aminoimidazole-4-carboxamide"],"weko_creator_id":"51","weko_shared_id":-1},"updated":"2025-01-29T11:55:35.088970+00:00"}