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タイトル: Synthesis of IB-01212 by multiple N-methylations of peptide bonds.
著者: Nabika, Ryota
Oishi, Shinya  kyouindb  KAKEN_id
Misu, Ryosuke
Ohno, Hiroaki  kyouindb  KAKEN_id
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 Ltd.
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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