Copper(II)-catalyzed transamination between pyruvate and hydrophobic pyridoxamine embedded in synthetic bilayer membranes.
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概要
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The copper(II)-catalyzed transamination of 4-aminomethyl-5-[(dihexadecylamino)methyl]-2-methyl-3-pyridinol [(PM)2C<SUB>16</SUB>] with sodium pyruvate was investigated in an aqueous medium at pH 6.9, μ 0.10 (KCl), and 30.0±0.1 °C in the presence of single-walled bilayer vesicles of <I>N</I>,<I>N</I>-dihexadecyl-<I>N</I><SUP>α</SUP>-[6-(trimethylammonio)hexanoyl]-L-alaninamide bromide [N<SUP>+</SUP>C<SUB>5</SUB>Ala2C<SUB>16</SUB>] and <I>N</I>,<I>N</I>-dihexadecyl-<I>N</I><SUP>α</SUP>-[6-(trimethylammonio)hexanoyl]-L-histidinamide bromide [N<SUP>+</SUP>C<SUB>5</SUB>His2C<SUB>16</SUB>]. The binding mode of the pyridoxamine moiety in the vesicles was clarified by comparing the reaction behavior of the (PM)2C<SUB>16</SUB>–pyruvate–Cu<SUP>II</SUP> system with that of the 4-aminomethyl-5-dodecylthiomethyl-2-methyl-3-pyridinol [(PM)C<SUB>12</SUB>]–pyruvate–Cu<SUP>II</SUP> system. The pyridoxamine moiety of (PM)2C<SUB>16</SUB> was more tightly anchored in the hydrogen-belt domain of the membranes than that of (PM)C<SUB>12</SUB> as confirmed by fluorescence polarization spectroscopy. The difference in binding mode between (PM)2C<SUB>16</SUB> and (PM)C<SUB>12</SUB> is reflected on the copper(II)-coordination equilibria for the formation of the copper(II)–ketimine intermediates. The copper(II)-catalyzed transamination of (PM)2C<SUB>16</SUB> with pyruvate in the N<SUP>+</SUP>C<SUB>5</SUB>His2C<SUB>16</SUB> vesicle was most enhanced among related reaction systems treated here. The rate enhancement was attributed to the favorable formation of the reactive 2:1 ketimine–copper(II) chelate and the general-base catalysis by the coordination-free imidazolyl group of the lipid.
著者
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Murakami Yukito
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
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KIKUCHI Jun-ichi
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University
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Akiyoshi Kazunari
Department Of Organic Material Institute Of Biomaterials And Bioengineering Tokyo Medical And Dental
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