Enantioselectivity enhancement in the deacylation of N-acyl amino acid esters by vesicular systems of long chain dipeptide nucleophiles and a cationic double chain surfactant.

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概要

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• The enantioselective deacylation of short chain and long chain <I>N</I>-acyl amino acid <I>p</I>-nitrophenyl esters, CH<SUB>3</SUB>(CH<SUB>2</SUB>)<I><SUB>n</SUB></I>CONH\overset*CH(R)–CO<SUB>2</SUB>C<SUB>6</SUB>H<SUB>4</SUB>NO<SUB>2</SUB>-<I>p</I> (R=C<SUB>6</SUB>H<SUB>5</SUB>CH<SUB>2</SUB>, (CH<SUB>3</SUB>)<SUB>2</SUB>CHCH<SUB>2</SUB>, CH<SUB>3</SUB>; <I>n</I>=0, 8, 12), was carried out at 4–25°C (pH 7.68) with the vesicular systems composed of <I>N</I>,<I>N</I>-didodecyl-<I>N</I>,<I>N</I>dimethylammonium bromide and long chain nucleophiles, <I>N</I><SUP>α</SUP>-dodecanoyl-L-histidine, <I>N</I><SUP>α</SUP>-(<I>N</I>-dodecanoyl-L-leucyl)-L-histidine(<B>3a</B>), <I>N</I><SUP>α</SUP>-(<I>N</I>-dodecanoyl-L-phenylalanyl)-L-histidine (<B>3b</B>), and <I>N</I>-(<I>N</I><SUP>α</SUP>-dodecanoyl-L-histidyl)-L-leucine (<B>3c</B>). Both the deacylation rate and the enantioselectivity were the largest in the deacylation of the substrates possessing a long <I>N</I>-acyl chain (<I>n</I>=8) with the efficient dipeptide nucleophiles (<B>3a</B> and <B>3b</B>) including the L-histidine moiety in their terminal position, and the neighboring amino acid binding to the L-histidine in <B>3a</B>, <B>3b</B>, and/or <B>3c</B> was found to play an important role in the enhancement of enantioselectivity. The lowering of the reaction temperature decreased the deacylation rate and increased the enantioselectivity. The maximum enantiomer rate ratio of 24.5 was obtained in the deacylation of <I>p</I>-nitrophenyl <I>N</I>-dodecanoylphenylalaninates with the dipeptide nucleophile <B>3b</B>. The characteristic features of the present reaction are discussed on the basis of kinetic parameters (binding constants and activation parameters) and isokinetic relationships.

• 公益社団法人 日本化学会の論文

著者

• OHKUBO Katsutoshi

  Department of Applied Chemistry and Biochemistry, Faculty of Engineering, Kumamoto University

• Nagasaki Masaru

  Department Of Health Science Faculty Of Psychological And Physical Science Aichi Gakuin University

• Matsumoto Noriko

  Department Of Agricultural Chemistry Faculty Of Agriculture Tottori University

• Yamaki Kazuhiro

  Department of Advanced Interdisciplinary Sciences, Graduate School of Engineering, Utsunomiya University, Utsunomiiya 321-8585, Japan

• Ogata Harumi

  Department of Synthetic Chemistry, Faculty of Engineering, Kumamoto University

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