Synthetic Study for Piperidamycins
Project/Area Number |
25750381
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Research Category |
Grant-in-Aid for Young Scientists (B)
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Allocation Type | Multi-year Fund |
Research Field |
Biomolecular chemistry
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Research Institution | Tohoku University |
Principal Investigator |
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Project Period (FY) |
2013-04-01 – 2015-03-31
|
Project Status |
Completed (Fiscal Year 2014)
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Budget Amount *help |
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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Keywords | 全合成 / デプシペプチド / 抗菌活性 / ピペラジン酸 / 環状デプシペプチド |
Outline of Final Research Achievements |
Synthetic studies of piperidamycin F and JBIR-39 were investigated. Acylation of gamma-hydroxypiperazic acid with acid chloride was efficiently performed in the presence of Sc(OTf)3 to afford the corresponding dipeptide in good yield. Synthesis of oligopiperazic acid structure, followed by removal of the protecting groups furnished the natural product JBIR-39. The structure of JBIR-39 was unequivocally determined, and its absolute configurations were established to be 2S, 6S, 8S, 11R, 16S, 21R, 26S, 27S. Based on the above results, synthesis of pipericamycin F was also investigated and preparation of its macrocyclic structure was carried out by macrolatonization using 2-methyl-6-nitrobenzoic anhydride (MNBA).
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Report
(3 results)
Research Products
(5 results)
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[Presentation] Synthetic Study of Piperidamycins2013
Author(s)
Naoki Sekioka, Masahito Yoshida, Miho Izumikawa, Motoki Takagi, Kazuo Shin-ya, and Takayuki Doi
Organizer
ICCA-13 (13th International Conference on the Chemistry of Antibiotics and other bioactive comopunds
Place of Presentation
山梨
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