| Project/Area Number |
13555245
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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 | 展開研究 |
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| Research Field |
有機工業化学
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| Research Institution | The University of Tokyo |
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Principal Investigator |
SAIGO Kazuhiko The University of Tokyo, Graduate School of Frontier Sciences, Professor, 大学院・新領域創成科学研究科, 教授 (80016154)
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| Co-Investigator(Kenkyū-buntansha) |
KINBARA Kazushi The University of Tokyo, Graduate School of Engineering, Lecturer, 大学院・工学系研究科, 講師 (30282578)
KOBAYASHI Yuka The University of Tokyo, Graduate School of Engineering, Research Associate, 大学院・工学系研究科, 助手 (80334316)
SAKAI Kenichi Yamakawa Chemical Industry Co., Ltd, Researcher, 研究開発部長(研究職)
酒井 建一 山川薬品工業株式会社, 研究開発部長(研究職)
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| Project Period (FY) |
2001 – 2004
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| Project Status |
Completed (Fiscal Year 2004)
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| Budget Amount *help |
¥13,400,000 (Direct Cost: ¥13,400,000)
Fiscal Year 2004: ¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2003: ¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 2002: ¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 2001: ¥4,700,000 (Direct Cost: ¥4,700,000)
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| Keywords | Racemic acid・racemic amine / Diastereomeric salt method / Conglomerate / Racemic compound / X-ray crystallographic analysis / CH-π相互作用 / キラル識別機構 |
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| Research Abstract |
We have recently reported that the probability for conglomerate formation is as high as 50% in the crystallizations of racemic acid and amine combinations, for which efficient enantioseparation is achieved by the diastereomeric salt method. In order to confirm the generality of the phenomenon, we tried to extend the crystallization to various kinds of racemic acid and amine combinations. However, only a few racemic and enantiopure forms of acids and amines, which have been resolved with high efficiency, were found, despite of heavy bibliographic search. Therefore, novel resolving agents suitable for the present study were developed prior to the examination. Six kinds of novel acidic resolving agents, which have a naphthalene and/or phosphonothioic skeleton, and four kinds of novel basic resolving agents, which have a benzindanylene and/or bishydroxy skeleton, were designed and synthesized for the present study.
Using various kinds of resolving agents, which were reported in literatures and developed in the present study, crystallizations of racemic acid and amine combinations were carried out in order to analyze the probability of the formation of conglomerate. As a result, we found that the probability was also about 50% for a wide variety of the combination, as we have reported. Furthermore, it was clarified that the determination of conglomerate could be carried out not only by X-ray crystallographic analysis but also by IR spectral and melting point analyzes of a single crystal and powdery micro crystals, which were obtained in the crystallization of a racemic acid and amine combination.
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