1988 Fiscal Year Final Research Report Summary
Synthesis of Polysaccharide Derivatives Having Optical Resolving Ability and Their Application for Liquid Chromatography
| Project/Area Number |
61470108
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
高分子合成
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| Research Institution | Osaka University |
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Principal Investigator |
OKAMOTO Yoshio Osaka University, Faculty of Engineering Science associate professor, 基礎工学部, 助教授 (60029501)
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| Project Period (FY) |
1986 – 1988
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| Keywords | Optical resolution / Chromatography / Chiral stationary phase / HPLC / Polysaccharide / Cellulose tribenzoate / Cellulose trisphenylcarbamate / アミローストリスフェニルカルバメート |
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| Research Abstract |
Cellulose was allowed to react with substituted benzoyl chlorides or substituted phenyl isocyanates to afford corresponding cellulose benzoates or cellulose phenylcarbamates. Each cellulose derivative was adsorbed on silica gel to be used as chiral stationary phase for high-performance liquid chromatography. Cellulose tribenzoate derivatives having an electron-donationg substituent exhibited better optical resolving ability than the derivatives having an electron-eithdrawing substituent. Cellulose tris(3-methylbenzoate) afforded a useful stationary phase which could resolve rather wide range of racemic compounds.
Optical resolving abilities of 30 cellulose trisphenylcarbamate derivatives were ecaluated in the same manner. The adilities were associated with the polarity of the carbamate group and high-order structure of the derivatives. The derivatives which showed a high ability were tris(3,5-dimenthylphenylcarbamate),tris(4-t-butylphenylcarbamate) and tris(3,5-dichlorophenylcarbamate). Particularly, the first two could resolve many drugs and afforded practically useful chiral packing materials which will be employed widely.
Fifteen amylose trisphenylcarbamate derivatives were also prepared and used as chiral stationary phases. Optical resolving abilities depended greatly on the substituents and tris(3,5-dimethylphenylcarbamate) exhibited high optical resolving ability which was different from that of the same derivative of cellulose, the amylose derivative resolved many enantiomers which could not be separated on cellulose tris(3,5-dimethylphenylcarbamate). These tris(3,5-dimethylphenylcarbamate)s were also supported on the silica gel with a greater diameter to be used as stationary phases for preparative separation. The resulting stationary phases were found to be useful for a large-scale separation.
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