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Diastereoselective Total Synthesis and Structural Confirmation of Surugamide F

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Title: Diastereoselective Total Synthesis and Structural Confirmation of Surugamide F
Authors: Kuranaga, Takefumi Browse this author
Fukuba, Atsuki Browse this author
Ninomiya, Akihiro Browse this author
Takada, Kentaro Browse this author
Matsunaga, Shigeki Browse this author
Wakimoto, Toshiyuki Browse this author →KAKEN DB
Keywords: marine natural product
structural elucidation
total synthesis
peptide
Issue Date: Jun-2018
Publisher: The Pharmaceutical Society of Japan
Journal Title: Chemical & pharmaceutical bulletin
Volume: 66
Issue: 6
Start Page: 637
End Page: 641
Publisher DOI: 10.1248/cpb.c18-00072
PMID: 29863066
Abstract: 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.
Type: article
URI: http://hdl.handle.net/2115/70954
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 脇本 敏幸

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