{"created":"2023-05-15T16:29:24.521289+00:00","id":142,"links":{},"metadata":{"_buckets":{"deposit":"43b856ab-dd4e-4960-aa93-c76eb7ea86f1"},"_deposit":{"created_by":2,"id":"142","owners":[2],"pid":{"revision_id":0,"type":"depid","value":"142"},"status":"published"},"_oai":{"id":"oai:nagasaki-u.repo.nii.ac.jp:00000142","sets":["10:11"]},"author_link":["645","648","649","646","647"],"item_2_biblio_info_6":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2020-10-13","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"20","bibliographicPageStart":"4667","bibliographicVolumeNumber":"25","bibliographic_titles":[{"bibliographic_title":"Molecules"}]}]},"item_2_description_4":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"We designed and synthesized helical short oligopeptides with an L-proline on the N-terminus and hydrocarbon stapling on \nthe side chain. Side-chain stapling is a frequently used method for the development of biologically active peptides. Side-chain stapling can stabilize the secondary structures of peptides, and, therefore, stapled peptides may be applicable to peptide-based organocatalysts. Olefin-tethered cis-4-hydroxy-L-proline 1 and L-serine 2 and 8, and (R)-αallyl-proline\n 18 were used as cross-linking motifs and incorporated into helical peptide sequences. The Z- and E-selectivities were observed for the ring-closing metathesis reactions of peptides 3 and 11 (i,i+1 series respectively, while no E/Z-selectivity was observed for that of 19 (i,i+3 series). The stapled peptide B' catalyzed the Michael addition reaction of 1-methylindole to α,β-unsaturated aldehyde, which was seven times faster than that of unstapled peptide B. Furthermore, the high catalytic activity was retained even at lower catalyst loadings \n(5 mol %) and lower temperatures (0 °C). The circular dichroism spectra of stapled peptide B' showed a right-handed helix with a higher intensity than that of unstapled peptide B. These results indicate that the introduction of side-chain stapling is beneficial for enhancing the catalytic activity of short oligopeptide catalysts.","subitem_description_type":"Abstract"}]},"item_2_description_63":{"attribute_name":"引用","attribute_value_mlt":[{"subitem_description":"Molecules, 25(20), art.no.4667; 2020","subitem_description_type":"Other"}]},"item_2_publisher_33":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"MDPI"}]},"item_2_relation_12":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_type":"isIdenticalTo","subitem_relation_type_id":{"subitem_relation_type_id_text":"10.3390/molecules25204667","subitem_relation_type_select":"DOI"}}]},"item_2_rights_13":{"attribute_name":"権利","attribute_value_mlt":[{"subitem_rights":"c2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open accessarticle distributed under the terms and conditions of the Creative Commons Attribution(CC BY) license (http://creativecommons.org/licenses/by/4.0/)."}]},"item_2_source_id_8":{"attribute_name":"EISSN","attribute_value_mlt":[{"subitem_source_identifier":"14203049","subitem_source_identifier_type":"ISSN"}]},"item_2_version_type_16":{"attribute_name":"著者版フラグ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_970fb48d4fbd8a85","subitem_version_type":"VoR"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Ueda, Atsushi"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Higuchi, Mei"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Sato, Kazuki"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Umeno, Tomohiro"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Tanaka, Masakazu"}],"nameIdentifiers":[{}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2020-12-16"}],"displaytype":"detail","filename":"molecules25_4667.pdf","filesize":[{"value":"2.4 MB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"molecules25_4667.pdf","url":"https://nagasaki-u.repo.nii.ac.jp/record/142/files/molecules25_4667.pdf"},"version_id":"87778411-9beb-4568-9dff-60129979d6f3"}]},"item_keyword":{"attribute_name":"キーワード","attribute_value_mlt":[{"subitem_subject":"Helix","subitem_subject_scheme":"Other"},{"subitem_subject":"Hydrocarbon stapling","subitem_subject_scheme":"Other"},{"subitem_subject":"L-proline","subitem_subject_scheme":"Other"},{"subitem_subject":"Michael addition","subitem_subject_scheme":"Other"},{"subitem_subject":"Organocatalyst","subitem_subject_scheme":"Other"},{"subitem_subject":"Peptide","subitem_subject_scheme":"Other"},{"subitem_subject":"Ring-closing metathesis","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":"Design and Synthesis of Helical N-Terminal l-Prolyl Oligopeptides Possessing Hydrocarbon Stapling","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Design and Synthesis of Helical N-Terminal l-Prolyl Oligopeptides Possessing Hydrocarbon Stapling"}]},"item_type_id":"2","owner":"2","path":["11"],"pubdate":{"attribute_name":"公開日","attribute_value":"2020-10-30"},"publish_date":"2020-10-30","publish_status":"0","recid":"142","relation_version_is_last":true,"title":["Design and Synthesis of Helical N-Terminal l-Prolyl Oligopeptides Possessing Hydrocarbon Stapling"],"weko_creator_id":"2","weko_shared_id":-1},"updated":"2023-05-16T04:21:19.514055+00:00"}