Development of Synthetic Oligomers Forming Higher-Order Structures by Self- and Molecular-Recognition Striving for Promotion of Chemical Reactions
| Project/Area Number |
25620129
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Bio-related chemistry
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| Research Institution | University of Toyama |
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Principal Investigator |
INOUYE Masahiko 富山大学, 大学院医学薬学研究部(薬学), 教授 (60211752)
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| Co-Investigator(Kenkyū-buntansha) |
ABE Hajime 富山大学, 大学院医学薬学研究部(薬学), 准教授 (10324055)
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| Project Period (FY) |
2013-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | ピリジン / フェノール / らせん構造 / 水素結合 / 自己会合 / 糖認識 / 人工オリゴマー |
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| Outline of Final Research Achievements |
We have developed "pyridine/phenol oligomer"s consisted of pyridine and phenol units linked at their 2,6-positions with acetylene bonds. The pyridine/phenol alternating 12- and 6-meric oligomers were prepared by Sonogashira reactions and their self-association and saccharide recognition were investigated.
In CDCl3, concentration dependence on 1H NMR spectra revealed that those oligomers show self-association of moderate strength. The Kdim were 350 and 34 M-1 for the 12- and 6-mer, respectively. The 12-mer exhibited much strong saccharide recognition ability. When octyl beta-D-glucopyranoside was added to a DCE solution of the 12-mer, a strong negative CD band was induced, and the Ka was 2.4 x 10^7 M-1. While, the shorter substrate 6-mer showed weaker saccaride recognition, showing a CD band of opposite sign.
These association are based on multipoint hydrogen bonding in a push-pull fashion, which was supported by the X-ray structure of a model compound binding with methanol.
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Report
(3 results)
Research Products
(10 results)
