Substrate Deacylation Mechanism of Serine beta-lactamases

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概要

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• The substrate deacylation mechanisms of serine-β-lactamases (classes A, C and D) wereinvestigated by theoretical calculations. The deacylation of class A proceeds via fourelementary reactions. The rate-determining process is the tetrahedral intermediate (TI)formation and the activation energy is 24.6 kcal/mol at the DFT level. The deacylation doesnot proceed only by Glu166, which acts as a general base, but Lys73 also participates in thereaction. The C3-carboxyl group of the substrate reduces the barrier height at the TIformation (substrate-assisted catalysis). In the case of class C, the deacylation consists of twoelementary processes. The activation energy of the TI formation has been estimated to be30.5 kcal/mol. Tyr150Oη is stabilized in the deprotonated state in the acyl-enzyme complexand works as a general base. This situation can exist due to the interaction with twopositively charged side chains of lysine (Lys67 and Lys315). The deacylation of class D alsoconsists of two elementary reaction processes. The activation energy of the TI formation is ca.30 kcal/mol. It is thought that the side chain of Lys70 is deprotonated and acts as a generalbase. When Lys70 is carbamylated, the activation energy is reduced to less than 20 kcal/mol.This suggests that the high hydrolysis activity of class D with carbamylated Lys70 is due tothe reduction of activation energy for deacylation. From these results, it is concluded that thecontribution of the lysine residue adjacent to the serine residue is indispensable for theenzymatic reactions by serine-β-lactamases.

• 2006-11-01

著者

• FUJII YASUYUKI

  Department of Ecological Engineering, Toyohashi University of Technology

• NEYA Saburo

  Department of Physical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University

• HOSHINO Tyuji

  Department of Physical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University

• HATA Masayuki

  Department of Physical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University

• Neya S

  Graduate School Of Pharmaceutical Sciences Chiba University

• Neya Saburo

  Department Of Physical Chemistry Graduate School Of Pharmaceutical Sciences Chiba University

• Neya Saburo

  Department Of Physical Chemistry Kyoto Pharmaceutical University

• Fujii Y

  Department Of Analytical Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University

• Hoshino T

  Department Of Physical Chemistry Graduate School Of Pharmaceutical Sciences Chiba University

• Hoshino Tyuji

  Department Of Physical Chemistry Graduate School Of Pharmaceutical Sciences Chiba University

• TANAKA Yoshikazu

  Department of Bioresource Development, Hiroshima Prefectural University

• TSUDA Minoru

  Department of Pharmacology and Toxicology, Kyorin University School of Medicine

• Tsuda M

  Chiba Univ. Chiba Jpn

• Tsuda Minoru

  Laboratory Of Biophysical Chemistry Faculty Of Pharmaceutical Sciences Chiba University

• Tsuda Minoru

  Laboratory Of Physical Chemistry Pharmaceutical Sciences Chiba University

• Neya Saburo

  Department Of Physical Chemistry Faculty Of Pharmaceutical Sciences Chiba University

• ISHIKAWA Hidenori

  Department of Physical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University

• ISHII Miho

  Department of Physical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University

• Hata M

  Department Of Physical Chemistry Graduate School Of Pharmaceutical Sciences Chiba University

• Hata Masayuki

  Department Of Biomedical Chemistry Graduate School Of Medicine The University Of Tokyo

• Fujii Yasuyuki

  Department Of Ecological Engineering Toyohashi University Of Technology

• Ishii M

  Department Of Physical Chemistry Graduate School Of Pharmaceutical Sciences Chiba University

• Mitsui Ikuo

  New Product Research Laboratories Iv Daiichi Pharmaceitucal Co. Ltd.

• Ishii Miho

  Department Of Chemistry Nara University Of Education

• Ishikawa Hidenori

  Department Of Physical Chemistry Graduate School Of Pharmaceutical Sciences Chiba University

• Tsuda Minoru

  Department Of Applied Physics And Chemistry The University Of Electro-communications

• Fujii Youichi

  Fac. Of Pharmaceutical Sciences Hokuriku Univ.

• Tanaka Yoshikazu

  Department Of Physical Chemistry Graduate School Of Pharmaceutical Sciences Chiba University

• Tanaka Yoshikazu

  Department Of Biology Faculty Of Science Osaka University

• 根矢 三郎

  Department of Physical Chemistry, Graduate School of Pharmaceutical Sciences, Chiba University

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