Study for rapid synthesis and mechanism elucidation of cyclic antifreeze glycopeptide
| Project/Area Number |
23350074
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemistry related to living body
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| Research Institution | Hokkaido University |
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Principal Investigator |
HINOU HIROSHI 北海道大学, 先端生命科学研究科(研究院), 准教授 (70333333)
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| Project Period (FY) |
2011-04-01 – 2014-03-31
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥19,240,000 (Direct Cost: ¥14,800,000、Indirect Cost: ¥4,440,000)
Fiscal Year 2013: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2012: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2011: ¥12,090,000 (Direct Cost: ¥9,300,000、Indirect Cost: ¥2,790,000)
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| Keywords | ペプチド環化 / 水素結合 / 配座解析 / 単結晶X線回折 / NMR / 糖ペプチド / 不凍活性 / AFGP / 環状ペプチド / 溶媒効果 / pKa / 環化率 / 環化反応 / 不凍糖タンパク質 / 結晶構造 / ＮＭＲ / 不凍糖ペプチド / 配座 |
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| Research Abstract |
Cyclic anti-freeze glydopeptide (AFGP) found by our group has different conformation from linear AFGP found from polar fish. To elucidate the structural feature of the cyclic AFGP, we developed novel cyclization method for peptide and glycopeptide by use of hydrogen-bonding property of fluorinated alcohols. Pure cyclic AFGP was obtained by the new method in high yield from solution of corresponding corresponding linear precursor. Interestingly, common cyclization method using DPPA induce C-terminal epimerization. NMR and X-ray crystallographic experiments for cyclic AFGP and corresponding cyclic peptide skeleton revealed anti-parallel beta-sheet structure of the both compound, and glycan modification induce a replacement of amino acid position in the structure.
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Report
(4 results)
Research Products
(48 results)
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[Journal Article] Microwave-assisted solid-phase synthesis of antifreeze glycopeptides2013
Author(s)
Izumi, R., Matsushita, T., Ohyabu, N., Fujitani, N., Naruchi, K., Shimizu, H., Tsuda, S., Hinou, H., and Nishimura, S.-I
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Journal Title
Chem. Eur. J.
Volume: 19
Issue: 12
Pages: 3913-3920
DOI
Related Report
Peer Reviewed
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