{"created":"2024-12-12T09:25:55.424987+00:00","id":2010867,"links":{},"metadata":{"_buckets":{"deposit":"c45e887c-00ad-424d-b9ac-b45963f1f9b4"},"_deposit":{"created_by":7,"id":"2010867","owners":[7],"pid":{"revision_id":0,"type":"depid","value":"2010867"},"status":"published"},"_oai":{"id":"oai:tokushima-u.repo.nii.ac.jp:02010867","sets":["1713853213384:1713853295607"]},"author_link":["1004","188","232"],"item_10001_biblio_info_7":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2023-03-15","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"26","bibliographicPageStart":"e202300799","bibliographicVolumeNumber":"29","bibliographic_titles":[{"bibliographic_title":"Chemistry- A European Journal","bibliographic_titleLang":"en"}]}]},"item_10001_description_5":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"A tyrosine (Tyr)- or tryptophan (Trp)-selective metal-free C−H sulfenylation reaction using an acid-activated Sacetamidomethyl cysteine (Cys) sulfoxide, Cys(Acm)(O), has been achieved. The dually protonated intermediate produced from the Cys(Acm)(O) under acidic conditions allows the sulfenylation of Tyr. Significantly, the reaction in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) mainly affords a Cys-Tyr-linked peptide even in the presence of Trp residues. In contrast, a Cys-Trplinked peptide was selectively obtained from the reaction in the presence of guanidine hydrochloride (Gn·HCl) under acidic conditions. Established Tyr- and Trp-selective sulfenylation methods were used in the Cys-Tyr stapling and Trp-lipidation of glucagon-like peptides 1 in a one-pot/stepwise manner. Investigation of the mechanism showed that orbital- and charge-controlled reactions are responsible for the Trp and Tyr selectivity, respectively.","subitem_description_language":"en","subitem_description_type":"Abstract"}]},"item_10001_publisher_8":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"Wiley-VCH","subitem_publisher_language":"en"}]},"item_10001_rights_15":{"attribute_name":"権利情報","attribute_value_mlt":[{"subitem_rights":"This is the peer reviewed version of the following article: Ohkawachi, Kento, Anzaki, Kaito, Kobayashi, Daishiro, Kyan, Ryuji, Yasuda, Takuma, Denda, Masaya, Harada, Norio, Shigenaga, Akira, Inagaki, Nobuya, Otaka, Akira, Chem. Eur. J. 2023, 29, 26, e202300799., which has been published in final form at https://doi.org/10.1002/chem.202300799. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.","subitem_rights_language":"en"}]},"item_10001_source_id_9":{"attribute_name":"収録物ID","attribute_value_mlt":[{"subitem_source_identifier":"15213765","subitem_source_identifier_type":"ISSN"},{"subitem_source_identifier":"AA11076269","subitem_source_identifier_type":"NCID"}]},"item_10001_version_type_20":{"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_1715043197608":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"open 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ダイシロウ","creatorNameLang":"ja"},{"creatorName":"コバヤシ, ダイシロウ","creatorNameLang":"ja-Kana"},{"creatorName":"Kobayashi, Daishiro","creatorNameLang":"en"}]},{"creatorNames":[{"creatorName":"キャン, リュウジ","creatorNameLang":"ja"},{"creatorName":"キャン, リュウジ","creatorNameLang":"ja-Kana"},{"creatorName":"Kyan, Ryuji","creatorNameLang":"en"}]},{"creatorNames":[{"creatorName":"ヤスダ, タクマ","creatorNameLang":"ja"},{"creatorName":"ヤスダ, タクマ","creatorNameLang":"ja-Kana"},{"creatorName":"Yasuda, Takuma","creatorNameLang":"en"}]},{"creatorAffiliations":[{"affiliationNameIdentifiers":[{"affiliationNameIdentifier":"","affiliationNameIdentifierScheme":"ISNI","affiliationNameIdentifierURI":"http://www.isni.org/isni/"}],"affiliationNames":[{"affiliationName":"","affiliationNameLang":"ja"}]}],"creatorNames":[{"creatorName":"傳田, 将也","creatorNameLang":"ja"},{"creatorName":"デンダ, マサヤ","creatorNameLang":"ja-Kana"},{"creatorName":"Denda, Masaya","creatorNameLang":"en"}],"familyNames":[{"familyName":"傳田","familyNameLang":"ja"},{"familyName":"デンダ","familyNameLang":"ja-Kana"},{"familyName":"Denda","familyNameLang":"en"}],"givenNames":[{"givenName":"将也","givenNameLang":"ja"},{"givenName":"マサヤ","givenNameLang":"ja-Kana"},{"givenName":"Masaya","givenNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"1004","nameIdentifierScheme":"WEKO"},{"nameIdentifier":"364585/profile-ja.html","nameIdentifierScheme":"徳島大学 教育研究者総覧","nameIdentifierURI":"http://pub2.db.tokushima-u.ac.jp/ERD/person/364585/profile-ja.html"},{"nameIdentifier":"00813891","nameIdentifierScheme":"e-Rad","nameIdentifierURI":"https://nrid.nii.ac.jp/ja/search/?qm=00813891"}]},{"creatorNames":[{"creatorName":"ハラダ, ノリオ","creatorNameLang":"ja"},{"creatorName":"ハラダ, ノリオ","creatorNameLang":"ja-Kana"},{"creatorName":"Harada, 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Akira","creatorNameLang":"en"}],"familyNames":[{"familyName":"重永","familyNameLang":"ja"},{"familyName":"シゲナガ","familyNameLang":"ja-Kana"},{"familyName":"Shigenaga","familyNameLang":"en"}],"givenNames":[{"givenName":"章","givenNameLang":"ja"},{"givenName":"アキラ","givenNameLang":"ja-Kana"},{"givenName":"Akira","givenNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"232","nameIdentifierScheme":"WEKO"},{"nameIdentifier":"10423394","nameIdentifierScheme":"e-Rad","nameIdentifierURI":"https://nrid.nii.ac.jp/ja/search/?qm=10423394"}]},{"creatorNames":[{"creatorName":"イナガキ, ノブヤ","creatorNameLang":"ja"},{"creatorName":"イナガキ, ノブヤ","creatorNameLang":"ja-Kana"},{"creatorName":"Inagaki, Nobuya","creatorNameLang":"en"}]},{"creatorAffiliations":[{"affiliationNameIdentifiers":[{"affiliationNameIdentifier":"","affiliationNameIdentifierScheme":"ISNI","affiliationNameIdentifierURI":"http://www.isni.org/isni/"}],"affiliationNames":[{"affiliationName":"","affiliationNameLang":"ja"}]}],"creatorNames":[{"creatorName":"大髙, 章","creatorNameLang":"ja"},{"creatorName":"オオタカ, アキラ","creatorNameLang":"ja-Kana"},{"creatorName":"Otaka, Akira","creatorNameLang":"en"}],"familyNames":[{"familyName":"大髙","familyNameLang":"ja"},{"familyName":"オオタカ","familyNameLang":"ja-Kana"},{"familyName":"Otaka","familyNameLang":"en"}],"givenNames":[{"givenName":"章","givenNameLang":"ja"},{"givenName":"アキラ","givenNameLang":"ja-Kana"},{"givenName":"Akira","givenNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"188","nameIdentifierScheme":"WEKO"},{"nameIdentifier":"121537/profile-ja.html","nameIdentifierScheme":"徳島大学 教育研究者総覧","nameIdentifierURI":"http://pub2.db.tokushima-u.ac.jp/ERD/person/121537/profile-ja.html"},{"nameIdentifier":"20201973","nameIdentifierScheme":"e-Rad","nameIdentifierURI":"https://nrid.nii.ac.jp/ja/search/?qm=20201973"}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_access","date":[{"dateType":"Available","dateValue":"2024-03-15"}],"displaytype":"detail","filename":"chemej_29_26_e202300799.pdf","filesize":[{"value":"1.16 MB"}],"format":"application/pdf","mimetype":"application/pdf","url":{"objectType":"fulltext","url":"https://tokushima-u.repo.nii.ac.jp/record/2010867/files/chemej_29_26_e202300799.pdf"},"version_id":"0eebd86d-b48f-4904-b2c7-387dc7ee0ccc"}]},"item_keyword":{"attribute_name":"キーワード","attribute_value_mlt":[{"subitem_subject":"peptide modification","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"Tyr sulfenylation","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"Trp sulfenylation","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"S-protected cysteine sulfoxide","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"SEAr reaction","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":"資源タイプ","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"Residue-selective C−H sulfenylation enabled by acid-activated S-acetamidomethyl cysteine sulfoxide with application to one-pot stapling and lipidation sequence","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Residue-selective C−H sulfenylation enabled by acid-activated S-acetamidomethyl cysteine sulfoxide with application to one-pot stapling and lipidation sequence","subitem_title_language":"en"}]},"item_type_id":"40001","owner":"7","path":["1713853295607"],"pubdate":{"attribute_name":"PubDate","attribute_value":"2023-03-17"},"publish_date":"2023-03-17","publish_status":"0","recid":"2010867","relation_version_is_last":true,"title":["Residue-selective C−H sulfenylation enabled by acid-activated S-acetamidomethyl cysteine sulfoxide with application to one-pot stapling and lipidation sequence"],"weko_creator_id":"7","weko_shared_id":-1},"updated":"2025-02-10T07:46:29.186105+00:00"}