DESIGN, SYNTHESIS, AND PROPERTIES OF CYCLOPHANES AS HOSTS HAVING ABILITY OF FORMING INCLUSION COMPLEXES
| Project/Area Number |
63470126
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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 |
Chemical pharmacy
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| Research Institution | FACULTY OF PHARMACEUTICAL SCIENCES, THE UNIVERSITY OF TOKYO |
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Principal Investigator |
KOGA Kenji Univ. of Tokyo Fac. Pharm. Sci. Professor, 薬学部, 教授 (10012600)
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| Co-Investigator(Kenkyū-buntansha) |
SASAKI Shigeki Univ. of Tokyo Fac. Pharm. Sci. Assistant Professor, 薬学部, 助手 (10170672)
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| Project Period (FY) |
1988 – 1989
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| Project Status |
Completed (Fiscal Year 1989)
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| Budget Amount *help |
¥7,600,000 (Direct Cost: ¥7,600,000)
Fiscal Year 1989: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1988: ¥4,700,000 (Direct Cost: ¥4,700,000)
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| Keywords | Water-soluble Cyclophanes / Molecular Recognition / Diarylmethane / Inclusion Complex / Host-Guest Chemistry / Inclusion of Cationic Guests / カチオン性シクロファン / アニオン性フィクロファン / ホストゲスト錯体 / クロマトグラフィー用担体 / 疎水性相互作用 / 電荷相互作用 |
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| Research Abstract |
Our earlier studies on cyclophanes such as QCP44 have suggested that they form inclusion complexes with anionic and neutral hydrophobic guests in aqueous solution. We intended to introduce the cyclophanes to stationary phase of column chromatography, and to design novel macrocyclic compounds as hosts for cationic guests.
The skeleton of QCP44 was introduced to agarose gel with amide bond, and some structural isomers, such as 1- or 2-naphthalane sulfonic acids, could be effectively separated by the column containing this gel.
Novel cyclophanes having carboxylates, ACP44 and ACP66, were synthesized, and were found to form stable 1:1 complexes with cationic guests. Stability constants (Ks) of their complexes were obtained using ^1H-NMR technique (Table 1). ACP44 exhibited the greatest value of K s for the complex with 1,4-bis(trimethylammoniummethyl)benzene. In contrast, ACP66 formed the most stable complex with 1,3-bis(trimethylammonium)propane.
Investigation on novel macrocycles for selective and efficient artificial catalysts as an enzyme model is now in progress.
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Report
(3 results)
Research Products
(16 results)
