Diastereoselective Total Synthesis and Structural Confirmation of Surugamide F
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- Kuranaga Takefumi
- Faculty of Pharmaceutical Sciences, Hokkaido University
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- Fukuba Atsuki
- Faculty of Pharmaceutical Sciences, Hokkaido University
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- Ninomiya Akihiro
- Graduate School of Agricultural and Life Sciences, The University of Tokyo
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- Takada Kentaro
- Graduate School of Agricultural and Life Sciences, The University of Tokyo
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- Matsunaga Shigeki
- Graduate School of Agricultural and Life Sciences, The University of Tokyo
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- Wakimoto Toshiyuki
- Faculty of Pharmaceutical Sciences, Hokkaido University
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Abstract
<p>Surugamide F is a linear decapeptide (1) isolated along with the cyclic octapeptides surugamides A–E (2–6), from a marine-derived Streptomyces species. The linear peptide 1 is produced by two nonribosomal peptide synthetases (NRPSs) encoded in adjacent open reading frames, which are further flanked by an additional pair of NRPS genes responsible for the biosyntheses of the cyclic peptides 2–6. While the cyclic peptides 2–6 were identified to be cathepsin B inhibitors, the biological activity of the new metabolite 1 still remained unclear. In order to elucidate its unique biosynthetic pathway and biological activity in detail, we planned to develop an efficient synthetic route toward 1. Here we report the diastereoselective total synthesis of 1, utilizing 9-fluorenylmethyloxycarbonyl (Fmoc)-based solid-phase peptide synthesis. During this study, we found that the structural correction of 1 was required, due to the mislabeling of the commercially obtained 3-amino-2-methylpropionic acid, and the true structure of 1 was corroborated by the chemical synthesis and chromatographic comparison.</p>
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 66 (6), 637-641, 2018-06-01
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390564237989384704
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- NII Article ID
- 130007382323
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- HANDLE
- 2115/70954
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- NDL BIB ID
- 029007084
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- PubMed
- 29863066
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- Text Lang
- en
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- Data Source
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- JaLC
- IRDB
- NDL
- Crossref
- PubMed
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed