Catalytic mechanism of angiotensin-converting enzyme and effects of the chloride ion

J Phys Chem B. 2013 Jun 6;117(22):6635-45. doi: 10.1021/jp400974n. Epub 2013 May 23.

Abstract

The angiotensin-converting enzyme (ACE) exhibits critical functions in the conversion of angiotensin I to angiotensin II and the degradation of bradykinin and other vasoactive peptides. As a result, the ACE inhibition has become a promising approach in the treatment of hypertension, heart failure, and diabetic nephropathy. Extending our recent molecular dynamics simulation of the testis ACE in complex with a bona fide substrate molecule, hippuryl-histidyl-leucine, we presented here a detailed investigation of the hydrolytic process and possible influences of the chloride ion on the reaction using a combined quantum mechanical and molecule mechanical method. Similar to carboxypeptidase A and thermolysin, the promoted water mechanism is established for the catalysis of ACE. The E384 residue was found to have the dual function of a general base for activating the water nucleophile and a general acid for facilitating the cleavage of amide C-N bond. Consistent with experimental observations, the chloride ion at the second binding position is found to accelerate the reaction rate presumably due to the long-range electrostatic interactions but has little influence on the overall substrate binding characteristics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis
  • Chlorides / chemistry*
  • Hydrolysis
  • Ions / chemistry
  • Molecular Dynamics Simulation
  • Oligopeptides / chemistry
  • Oligopeptides / metabolism
  • Peptidyl-Dipeptidase A / chemistry
  • Peptidyl-Dipeptidase A / metabolism*
  • Protons
  • Quantum Theory
  • Substrate Specificity
  • Water / chemistry
  • Water / metabolism

Substances

  • Chlorides
  • Ions
  • Oligopeptides
  • Protons
  • Water
  • hippuryl-histidyl-leucine
  • Peptidyl-Dipeptidase A