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j.bmc.2014.08.036.pdf | 341.46 kB | Adobe PDF | 見る/開く |
タイトル: | Synthesis of IB-01212 by multiple N-methylations of peptide bonds. |
著者: | Nabika, Ryota Oishi, Shinya https://orcid.org/0000-0002-2833-2539 (unconfirmed) Misu, Ryosuke Ohno, Hiroaki https://orcid.org/0000-0002-3246-4809 (unconfirmed) Fujii, Nobutaka |
著者名の別形: | 大石, 真也 |
キーワード: | Depsipeptide Macrolactonization N-Methylamino acid N-methylation |
発行日: | 8-Sep-2014 |
出版者: | Elsevier BV |
誌名: | Bioorganic & medicinal chemistry |
巻: | 22 |
号: | 21 |
開始ページ: | 6156 |
終了ページ: | 6162 |
抄録: | There are many natural peptides with multiple N-methylamino acids that exhibit potent attractive biological activities. N-methylation of a peptide bond(s) is also one of the standard approaches in medicinal chemistry of bioactive peptides, to improve the potency and physicochemical properties, especially membrane permeability. In this study, we investigated a facile synthesis process of N-methylated peptides via simultaneous N-methylation of several peptide bonds in the presence of peptide bonds that were not to be methylated. As a model study, we investigated the synthesis of the antiproliferative depsipeptide, IB-01212. We used a pseudoproline to protect the non-methylated peptide bond during a simultaneous N-methylation with MeI-Ag[2]O. Using further manipulations including a dimerization/cyclization process, IB-01212 and its derivatives were successfully synthesized. A preliminary structure-activity relationship study demonstrated that the symmetric structure contributed to the potent cytotoxic activity of IB-01212. |
著作権等: | © 2014 Elsevier Ltd. This is not the published version. Please cite only the published version. 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。 |
URI: | http://hdl.handle.net/2433/191267 |
DOI(出版社版): | 10.1016/j.bmc.2014.08.036 |
PubMed ID: | 25261926 |
出現コレクション: | 学術雑誌掲載論文等 |
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