2001 Fiscal Year Final Research Report Summary
High-Performance Chiral Separation Systems Based on Polysaccharide Derivatives
| Project/Area Number |
10208206
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| Research Category |
Grant-in-Aid for Scientific Research on Priority Areas (B)
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| Allocation Type | Single-year Grants |
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| Research Institution | Nagoya University |
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Principal Investigator |
OKAMOTO Yoshio Grad. School of Eng., Nagoya Univ., Professor, 工学研究科, 教授 (60029501)
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| Co-Investigator(Kenkyū-buntansha) |
YOSHIKAWA Masakazu Kyoto Institute of Technology, Professor, 高分子学科, 教授 (60158417)
MIYATA Mikiji Osaka Univ., Professor, 大学院・工学研究科, 教授 (90029322)
YASHIMA Eiji Grad. School of Eng., Nagoya Univ., Professor, 工学研究科, 教授 (50191101)
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| Project Period (FY) |
1998 – 2000
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| Keywords | Polysaccharide / Chiral Discrimination / HPLC / Chiral Stationary Phase / Crystalline Inclusion / Steroidal Bile Acid / Molecular Imprinting / Membrane |
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| Research Abstract |
1. Cyclohexylcarbamates of cellulose and amylose were prepared and their resolving abilities for enantiomers were evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). The CSPs showed high resolving abilities, and could also be used for thin-layer chromatography (TLC). These derivatives were soluble in chloroform and exhibited chiral discrimination to some chiral compounds in ^1H NMR spectroscopy as well as in HPLC.
2. Chitin is a readily available polysaccharide with 1,4-glycosidic linkage as well as cellulose and amylose. However, until recently this polysaccharide had not successfully been used for the preparation of CSPs for HPLC. We have found a suitable method for the preparation of chitin carbamates, such as 3,5-dimethyl, 4-chloro and 4-trifluoromethylphenylcarbamates, with relatively high chiral recognition abilities. The CSPs of chitin 3,5-dimethyl and 3,5-dichlorophenylcarbamates can be used in the presence of chloroform as a component
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of eluents owing to their poor solubilities in the eluent.
3. We studied the molecular recognition in crystalline inclusion compounds of bile acids and their derivatives. The existence of many asymmetric carbons and multiple hydrogen bonding groups enabled us to check notable effects of any point mutations of their molecular structures on chiral recognition. Recrystallization of the derivatives from liquid organic compounds afforded inclusion crystals suitable for single-crystal X-ray analysis. The host assemblies mostly have bilayered structures which involve one-dimensional spaces with some pockets. This research led to the reasonable interpretation of molecular recognition in size, shape, polarity and chirality.
4. We have found that a membrane which contains an oligopeptide residue from an L-amino acid and is imprinted by a L-amino acid derivative recognizes the L-isomer in preference to the corresponding D-isomer, and vice versa. Enantioselective electrodialysis was attained with the membranes reflecting their adsorption selectivity. Less
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