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2017 Fiscal Year Final Research Report

Synthetic study of antibiotic cyclopeptides toward eluciation of structure-activity relationships

Research Project

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Project/Area Number 15K01796
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Biomolecular chemistry
Research InstitutionTohoku University

Principal Investigator

Yoshida Masahito  東北大学, 薬学研究科, 助教 (80511906)

Project Period (FY) 2015-04-01 – 2018-03-31
Keywords環状ペプチド / 抗菌活性 / 全合成 / 構造活性相関
Outline of Final Research Achievements

In this research, total synthesis of potent antibiotic cyclodepsipeptide piperidamycins was investigated. Originally developed Sc(OTf)3-catalyzed acylation of gamma-hydroxypiperazic acid derivative with piperazic chloride afforded the corresponding dipeptide, which was sequentially coupled with piperazic chlorides to provide desired tetrapiperazic acid derivative. After elongation to the hexapeptide by condensation with corresponding amino acids, removal of the protecting groups at N- and C-terminus afforded the cyclization precursor. Finally, macrolactonization using MNBA/DMAPO under high dilution conditions, followed by global deprotection of the protecting groups furnished plausible structure of piperidamycin F.

Free Research Field

生物分子化学,有機合成化学

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Published: 2019-03-29   Modified: 2020-03-30  

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