1988 Fiscal Year Final Research Report Summary
Molecular Recognition Applying Self-Association Based on Hydrogen Bond
| Project/Area Number |
62570973
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Physical pharmacy
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| Research Institution | Tokyo College of Pharmacy |
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Principal Investigator |
HARA Shoji Tokyo College of Pharmacy, Professor, 薬学部, 教授 (40057287)
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| Co-Investigator(Kenkyū-buntansha) |
DOBASHI Yasuo Tokyo College of Pharmacy, 薬学部, 助手 (30164099)
DOBASHI Akira Tokyo College of Pharmacy, 薬学部, 講師 (40138962)
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| Project Period (FY) |
1987 – 1988
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| Keywords | amino acid derivatives / hydrogen bond / diastereomeric association / self-induced non-equivalence in NMR / 不斉識別 |
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| Research Abstract |
Mechanisms of hydrogen bond associations of amino acid derivatives were investigated in order to develop the method for molecular recognition applying self-association. NMR and IR studies indicated that an enantiomeric pair of amino acid(valine or leucine) tert-butylester forms cyclic dimers through two sets of hydrogen bonds between amide NH and carbony1 C=0 in aprotic solvents such as chloroform and carbon tertachloride. Stability differences between L-L(homo) dimers and L-D(hetero) dimers were also examined. It was found that the homodimers were energetically preferred to the heterodimers.
The observed enantioselectivity in self-association of amino acid derivatives suggests that valine diamide derivatives are the most promising candidates for incorporating the chiral stationary phase (CSP) which allows the optical resolutions of a wide range of amino acid derivatives. On the basis of this concept, CSP derived from valine diamide was designed and synthesized. This CSP was found to be capable of broad spectrum resoultion of enantiomers including amino acid, hydroxy carboxylic acid, amine, and amino alcohol derivatives.
The associated strucures of amino acid derivatives which is responsible for enantioselectivity in self-association of these derivatives was further investigeted using N-methy1 amino acid derivatives. As a result, the association between C5 and C7 sites of amino acid diamides play an important role in the enantioselection of the derivatives.
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Research Products
(4 results)
