On a possible neutral charge state for the catalytic dyad in β-secretase when bound to hydroxyethylene transition state analogue inhibitors

J Med Chem. 2011 Apr 28;54(8):3081-5. doi: 10.1021/jm101568y. Epub 2011 Mar 31.

Abstract

β-Secretase is one of the aspartic proteases involved in the formation of amyloid plaques in Alzheimer's disease patients. Our previous results using a combination of surface plasmon resonance experiments with molecular modeling calculations suggested that the Asp dyad in β-secretase bound to hydroxylethylene containing inhibitors adopts a neutral charged state. In this work, we show that the Asp dyad diprotonated state reproduced the binding ranking of a set of these inhibitors better than alternative protonation states.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amyloid Precursor Protein Secretases / metabolism*
  • Catalysis
  • Ethylenes / metabolism*
  • Hydrogen Bonding

Substances

  • Ethylenes
  • hydroxyethylene
  • Amyloid Precursor Protein Secretases