Catalytic efficiency of functionalized vesicles in the transamination of pyridoxal-5'-phosphate with a hydrophobic amino acid.
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概要
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The transamination reaction of pyridoxal-5′-phosphate (PLP) with <I>N</I>-dodecyl-L-alaninamide (AlaC<SUB>12</SUB>) was investigated in an aqueous phosphate–borate buffer at pH 7.0, μ 0.10 (KCl), and 30.0±0.1 °C in the presence of single-walled vesicles of <I>N</I>,<I>N</I>-ditetradecyl-<I>N</I><SUP>α</SUP>-(6-trimethylamnioniohexanoyl)-L-histidinamide bromide(N<SUP>+</SUP>C<SUB>5</SUB>His2C<SUB>14</SUB>). The electrostatic and hydrophobic interactions between the vesicles and the reactants resulted in incorporation of PLP and AlaC<SUB>12</SUB> into polar and hydrophobic domains of the vesicles, respectively, in the Schiff-base formation process. The isomerization of the aldimine Schiff-base to the corresponding ketimine Schiff-base was confirmed to be the rate-determining step in the transamination process. The reaction site in the vesicular system was found to be equivalent in polarity to dioxane–water (7:3 v/v). However, the overall reaction rate in the vesicles was enhanced 230-fold relative to that in dioxane–water (7:3 v/v). A hydrophobic and suitably polar microenvironment constructed at the reaction site is responsible for such a marked rate-enhancement. In addition, each vesicle of N<SUP>+</SUP>C<SUB>5</SUB>His2C<SUB>14</SUB> provided functional (imidazolyl) groups in its hydrogen-belt domain to catalyze the intramolecular pro to tropic shift to yield the ketimine Schiff-base. The microenvironmental effects of molecular assemblies of <I>N</I>,<I>N</I>-ditetradecyl-<I>N</I><SUP>α</SUP>-(6-trimethylammoniohexanoyl)-L-alaninamide bromide and CTAB on the overall transamination were also discussed.
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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Nakano Akio
Department of Chemistry, Faculty of Science, Kyushu University
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