1999 Fiscal Year Final Research Report Summary
Regulation of supramolecule systems included of hydrogen bond in aqueoous solution
| Project/Area Number |
09680579
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioorganic chemistry
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| Research Institution | Tokyo Institute of Polytechnics |
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Principal Investigator |
TAKAHASHI(YAMANOBE) Keiko (高橋 圭子) Tokyo Institute of Polytechnics Associate Professor, 工学部, 助教授 (00188004)
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| Project Period (FY) |
1997 – 1999
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| Keywords | cyclodextrin / hydrogen bond / self-organization / molecular block / NMR / supramolecule / recognition of succharide |
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| Research Abstract |
Supramolecular chemistry is that discipline of chemistry which involves all intermolecular interactions where covalent bonds are not established between interacting species. The majority of these interactions is of the host-guest type and in non-aqueous solution. In nature, supramolecular systems are regulated in the presence of water.
Cyclodextrins (CDs) have been known to be the most important ones, because they form inclusion complexes with a variety of aromatic compounds in aqueous solution. Early stages in CD chemistry presented a wide range of chemists with the very impressive concept of a host-guest complex described as a ball in a bottomless pail. To compose a more organized system using simply modified CDs, the important factor is the combination of "flexible" groups and "rigid" groups. Aromatic groups on CD through a flexible arm usually form intramolecular complexes. Potential formation of intramolecular inclusion complexes in other peptide-CD as evidenced by NMR study has been reported. To expand CD chemistry to realize unique superstructures in the solution for a substituted CD derivative that behaves both as host and as a guest, such that a substituent on the primary face of one molecule enters the cavity of the CD ring of a neighboring molecule, an aliphatic hydrophobic group, such as the tert-butoxycarbonyl group (Boc group) is introduced CD.The length of an arm between the N-tert-butoxycarbonyl group and the C6 position on the glucose ring was that of -NH-C -CO-NH-. Modified CDs having a longer arm form intramolecular rather than intermolecular complexes. Some CDs form "pseudo polymers" with inclusion phenomenon.
CyD has been found to selectively bind with excess molar amounts of D-fucose and precipitates in a neutral aqueous solution. In other words, CyD discriminates the optical isomers of D-fucose.
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