| Project/Area Number |
10460046
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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 |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
OHRUI Hiroshi Graduate school of Agriculturalscience, TOHOKU UNIVERSITY, professor, 大学院・農学研究科, 教授 (20100050)
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| Co-Investigator(Kenkyū-buntansha) |
AKASAKA Kazuaki Graduate school of Agriculturalscience, TOHOKU UNIVERSITY, Assistant professor, 大学院・農学研究科, 助教授 (10201881)
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| Project Period (FY) |
1998 – 2000
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| Project Status |
Completed (Fiscal Year 2000)
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| Budget Amount *help |
¥9,900,000 (Direct Cost: ¥9,900,000)
Fiscal Year 2000: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1999: ¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 1998: ¥5,700,000 (Direct Cost: ¥5,700,000)
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| Keywords | discrimination of remote chirality / branched fatty acid / branched alcohol / chiral discrimination / fluorescent chiral derivatization reagent / ^1H-NMR / HPLC / 蛍光性不斉誘導化試薬 / 高感度蛍光検出 / (S)-2AP-OTf / (S)-1A2P-OTf / CH-π相互作用 / ゴーシュ効果 |
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| Research Abstract |
We have open a way to the chiral discrimination of enantiomers having chiral center far remote from the diastereomeric-derivatizable functional groups that has been thought impossible for long time. Thus, a new chiral derivatization reagents, (R)-and (S)-2A-1P-O-Tf (1) and (R)-and (S)-1A-2P-O-Tf (2) are developed and the chiral discriminations of the carboxylic acids with methyl branching at from 2 to 11 by ^1H-NMR and those from 2 to 8 by HPLC were attainedby labelling with 1 and 2. A new reagent to improve the shortcomings of 1 and 2, (R,R)-and (S,S)-2A-CH-OH (3), was developed and the chiral discrimination of methyl branched fatty acids with branching from 2 to 24 was attained with 3. By these system, the absolute configuration of ceramides, gangliosides, and glycerol were determined using μ〜ng of samples.
Chiral derivatization reagents for chiral alcohols (R,R)-and (S,S)-2A-CH-COOH (4) and 3,4,6-O-Ac-2A-2d-β-Glu-Br (5) were prepared, and a system for the determination of absolute configuration of chiral alcohols by use of 4 was developed.
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