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タイトル: | Catalytic dehydrative peptide synthesis with gem-diboronic acids |
著者: | Michigami, Kenichi Sakaguchi, Tatsuhiko Takemoto, Yoshiji |
著者名の別形: | 道上, 健一 坂口, 達彦 竹本, 佳司 |
キーワード: | organoboron catalyst gem-diboronic acid dehydrative amidation |
発行日: | 3-Jan-2020 |
出版者: | American Chemical Society |
誌名: | ACS Catalysis |
巻: | 10 |
号: | 1 |
開始ページ: | 683 |
終了ページ: | 688 |
抄録: | Alkane-gem-diboronic acids have emerged as versatile organoboron catalysts for dehydrative amidation of α-amino acids. A phenol-substituted multiboron catalyst with a B–C–B structure outperformed simple arylboronic acids in the condensation of α-amino acids with suppressed epimerization of electrophiles. gem-diboronic acid catalysis were compatible with various O, N, and S-functionalized α-amino acids bearing N-protecting groups including common carbamates used in peptide synthesis (Boc, Cbz, Fmoc). N-trifluoroacetyl protection enabled an unprecedented catalytic dehydrative peptide synthesis at room temperature. Preliminary mechanistic studies revealed carboxylate-binding nature of gem-diboronic acids, orthogonal to the activation of carboxylic acids by arylboronic acids. The distinctive reactivity of the gem-diboronic acids would open prospects for mild catalytic peptide condensation. |
著作権等: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.9b03894. The full-text file will be made open to the public on 12 December 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. 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/2433/245796 |
DOI(出版社版): | 10.1021/acscatal.9b03894 |
出現コレクション: | 学術雑誌掲載論文等 |
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