The stereoselective deacylation of long-chain amino acid esters by comicelles of N-acyl-L-histidine and various cationic surfactants.
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概要
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The stereoselective deacylation of H–(CH<SUB>2</SUB>)\underset<I>n</I>－1—CONHCH(R)CO<SUB>2</SUB>–C<SUB>6</SUB>H<SUB>4</SUB>NO<SUB>2</SUB>-<I>p</I> (R=CH<SUB>3</SUB>, CH(CH<SUB>3</SUB>)<SUB>2</SUB>, CH<SUB>2</SUB>CH(CH<SUB>3</SUB>)<SUB>2</SUB>, and C<SUB>6</SUB>H<SUB>5</SUB>CH<SUB>2</SUB>; <I>n</I>=2–16) with <I>N</I>-acyl-L-histidine (acyl=octanoyl, dodecanoyl, and hexadecanoyl) and cationic surfactants (C<I><SUB>m</SUB></I>H<SUB>2<I>m</I>+1</SUB>\overset+N(CH<SUB>3</SUB>)<SUB>2</SUB>R X; (R,X,m)=(CH<SUB>3</SUB>,Br,16), (C<SUB>2</SUB>H<SUB>5</SUB>,Br,16), (C<SUB>6</SUB>H<SUB>5</SUB>CH<SUB>2</SUB>,Cl,16), and (\overset*CH(CH<SUB>3</SUB>)C<SUB>6</SUB>H<SUB>5</SUB>,Br, 14–18) was examined with particular reference to the structural effects of surfactants, nucleophiles, and substrates on both the deacylation rates and the stereoselectivity. The cationic surfactant, R-(+)-C<SUB>16</SUB>H<SUB>33</SUB>\overset+N(CH<SUB>3</SUB>)<SUB>2</SUB>\overset*CH(CH<SUB>3</SUB>)C<SUB>6</SUB>H<SUB>5</SUB> Br, which possesses the hydrophobic and chiral groups near the polar head, formed the stereoselectively most effective comicelles with <I>N</I>-dodecanoyl-L-histidine. The order of stereoselectivity observed in the deacylation of the amino acid esters including the identical acyl chain length (n), phenylalanine>leucine>alanine∼valine. suggested steric effects of the substituent bound to the asymmetric carbon atom of the substrate on the stereoselectivity. The highest stereoselectivity (enantiomer rate ratio=4.4 at 25 °C under pH 7.61) was observed in the deacylation of the <I>N</I>-decanoylphenylalanine <I>p</I>-nitrophenyl ester, involving an appropriately long acyl chain.
著者
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OHKUBO Katsutoshi
Department of Applied Chemistry and Biochemistry, Faculty of Engineering, Kumamoto University
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UEOKA Ryuichi
Department of Applied Life Science, Sojo University
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Sugahara Kiyoshi
Department Of Biology Faculty Of Science Kyushu University
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Ohta Hidefumi
Department Of Quantum Process Graduate School Of Engineering Science Kyushu University
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Tokuda Katsuro
Department of Industrial Chemistry, Kumamoto Institute of Technology
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