2000 Fiscal Year Final Research Report Summary
Studies on Development of High-sensitive Optical Purity Determination Reagents Using Optically Active Fluorescent Quinoxalines
| Project/Area Number |
11650876
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Seikei University |
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Principal Investigator |
KATOH Akira Seikei University, 工学部, 教授 (00167339)
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| Project Period (FY) |
1999 – 2000
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| Keywords | quinoxaline / fluorescent diastereomer / quantum yield / reversed-phase column / HPLC / detection limit / optical purity determination reagent |
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| Research Abstract |
In this project, I investigated synthesis of optically active fluorescent quinoxalines and their application to high-sensitive optical purity determination reagents for racemic carboxylic acids.
1. Chiral 2,3-dimorpholinoquinoxalines bearing amino acid residues at C-6 position were newly synthesized. 2. The derivatization of D,L-naproxen, -ibuprofen, and -2-phenylpropionic acid with chiral quinoxalines bearing L-amino acid residues was carried out by using the Mukaiyama method to give the diastereomers, which emitted intense fluorescence. 3. Fluorescence maxima of the diastereomers appeared around 440 nm when the excitation wavelength of about 370 nm was applied. 4. The fluorescence intensity in aqueous MeCN solution was remarkably decreased compared with that in MeCN.5. The quantum yield of fluorescence was measured to be 0.052 by using the relative quantum yield measurement with anthracene as a standard. 6. All the diastereomers derived from D,L-naproxen, -ibuprofen, and -2-phenylpropionic acid with chiral quinoxaline bearing the L-prolin residue were clearly separated within 16 min on reversed-phase (Finepak SIL C_<18>S) HPLC equipped with a fluorescence detector. 7. The detection limit of the diastereomer was estimated to be 5 pmol/10 μl injection volume on the S/N ratio of 5.
In conclusion, optically active fluorescent quinoxalines bearing the amino acid residue were demonstrated to be applicable to new high-sensitive optical purity determination reagents for chiral carboxylic acids.
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