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タイトル: | Design and synthesis of amidine-type peptide bond isosteres: application of nitrile oxide derivatives as active ester equivalents in peptide and peptidomimetics synthesis. |
著者: | Inokuchi, Eriko Yamada, Ai Hozumi, Kentaro Tomita, Kenji Oishi, Shinya https://orcid.org/0000-0002-2833-2539 (unconfirmed) Ohno, Hiroaki https://orcid.org/0000-0002-3246-4809 (unconfirmed) Nomizu, Motoyoshi Fujii, Nobutaka |
著者名の別形: | 大石, 真也 藤井, 信孝 |
発行日: | 7-May-2011 |
出版者: | Royal Society of Chemistry |
誌名: | Organic & biomolecular chemistry |
巻: | 9 |
号: | 9 |
開始ページ: | 3421 |
終了ページ: | 3427 |
抄録: | Amidine-type peptide bond isosteres were designed based on the substitution of the peptide bond carbonyl (C=O) group with an imino (C=NH) group. The positively-charged property of the isosteric part resembles a reduced amide-type peptidomimetic. The peptidyl amidine units were synthesized by the reduction of a key amidoxime (N-hydroxyamidine) precursor, which was prepared from nitrile oxide components as an aminoacyl or peptidyl equivalent. This nitrile oxide-mediated C-N bond formation was also used for peptide macrocyclization, in which the amidoxime group was converted to peptide bonds under mild acidic conditions. Syntheses of the cyclic RGD peptide and a peptidomimetic using both approaches, and their inhibitory activity against integrin-mediated cell attachment, are presented. |
著作権等: | © The Royal Society of Chemistry 2011 この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/156967 |
DOI(出版社版): | 10.1039/c0ob01193b |
PubMed ID: | 21423919 |
出現コレクション: | 学術雑誌掲載論文等 |
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