Aggregation behavior of amphiphiles functionalized with dipeptide segments and enantioselective ester hydrolysis in their bilayer membranes.
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概要
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Four amphiphiles having dipeptide segments, which consist of one histidyl residue and another amino acid residue, and the dihexadecyl moiety for the double-chain segment (N<SUP>+</SUP>C<SUB>5</SUB>AlaHis2C<SUB>16</SUB>, N<SUP>+</SUP>C<SUB>5</SUB>LeuHis2C<SUB>16</SUB>, N<SUP>+</SUP>C<SUB>5</SUB>PheHis2C<SUB>16</SUB>, and N<SUP>+</SUP>C<SUB>5</SUB>HisAla2C<SUB>16</SUB>) were synthesized, and the aggregate morphology of them was characterized by electron microscopy and differential scanning calorimetry. The amphiphiles, which have the histidyl residue bound to the dihexadecylamine component (N<SUP>+</SUP>C<SUB>5</SUB>AlaHis2C<SUB>16</SUB>, N<SUP>+</SUP>C<SUB>5</SUB>LeuHis2C<SUB>16</SUB>, N<SUP>+</SUP>C<SUB>5</SUB>PheHis2C<SUB>16</SUB>) formed both multi- and single-walled aggregates in the aqueous dispersion state, while their sonicated solutions involved only single-walled vesicles. On the other hand, the amphiphile, which has the alanyl residue bound to the dihexadecylamine component (N<SUP>+</SUP>C<SUB>5</SUB>HisAla2C<SUB>16</SUB>) afforded tubular aggregates in the aqueous dispersion. The hydrolysis of enantiomeric esters of various hydrophobic nature, which was carried out in the single-walled vesicles, showed relatively small enantioselectivity. The reasons for such catalytic performance of the vesicles were discussed from the kinetic and mechanistic viewpoints; the kinetic analysis being carried out on the basis of the organic pseudo-phase concept.
著者
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Murakami Yukito
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
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Akiyoshi Kazunari
Department Of Organic Material Institute Of Biomaterials And Bioengineering Tokyo Medical And Dental
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Imori Toru
Department Of Electrical And Computer Engineering Nagoya Institute Of Technology:central Research La
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Nakano Akio
Department of Chemistry, Faculty of Science, Kyushu University
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Imori Toru
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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Ikeda Hidetsugu
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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