Hydrolase Models of Bis-Quaternary Ammonium Salts

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  • TAKEZAWA Tsuneo
    Department of Applied Chemistry, Faculty of Engineering, Kogakuin University
  • YODA Yuki
    Department of Applied Chemistry, Faculty of Engineering, Kogakuin University
  • KOYAMA Yusuke
    Department of Applied Chemistry, Faculty of Engineering, Kogakuin University
  • OHKATSU Yasukazu
    Department of Applied Chemistry, Faculty of Engineering, Kogakuin University

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Other Title
  • ビス第四級アンモニウム塩型加水分解酵素モデル
  • ビス ダイ4キュウ アンモニウムエンガタ カスイ ブンカイ コウソ モデル キシツ ノ シキベツ
  • -Recognition of Substrate
  • -基質の識別-

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Abstract

In this study, amphiphiles possessing two equivalent ammonium groups substituted with one methyl and two dodecyls, and a connecting chain were synthesized; the connecting chain consisting of such hydrophilic group that hydroxyl group and ether linkage were introduced on and into the alkanediyl chain. This paper reports the structural effects of a segment connecting two quaternary ammonium salts on the recognition of amino acids in the hydrolysis of amino acid esters using bis-quaternary ammonium salts as catalysts. The hydrophilic nature of the connecting chain was found to have effect on substrate recognition. A connecting chain with high HLB (Hydrophile-Lipophile Balance) increased the hydrolyzing rate of a hydrophilic substrate but decreased that of a hydrophobic substrate. From the relationship between the rate constant k2 and Michaelis constant Km in the hydrolysis of amino acid esters, clearly shows that the uptake process of substrate is a rate-determining step, that is, a substrate is recognized by connecting chain in the uptake step. The connecting chain may thus be considered to form a pocket capable of discerning the hydrophilic nature of a substrate.

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