Characterization of the channel constriction allowing the access of the substrate to the active site of yeast oxidosqualene cyclase

PLoS One. 2011;6(7):e22134. doi: 10.1371/journal.pone.0022134. Epub 2011 Jul 21.

Abstract

In oxidosqualene cyclases (OSCs), an enzyme which has been extensively studied as a target for hypocholesterolemic or antifungal drugs, a lipophilic channel connects the surface of the protein with the active site cavity. Active site and channel are separated by a narrow constriction operating as a mobile gate for the substrate passage. In Saccharomyces cerevisiae OSC, two aminoacidic residues of the channel/constriction apparatus, Ala525 and Glu526, were previously showed as critical for maintaining the enzyme functionality. In this work sixteen novel mutants, each bearing a substitution at or around the channel constrictions, were tested for their enzymatic activity. Modelling studies showed that the most functionality-lowering substitutions deeply alter the H-bond network involving the channel/constriction apparatus. A rotation of Tyr239 is proposed as part of the mechanism permitting the access of the substrate to the active site. The inhibition of OSC by squalene was used as a tool for understanding whether the residues under study are involved in a pre-catalytic selection and docking of the substrate oxidosqualene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalytic Domain*
  • Enzyme Inhibitors / pharmacology
  • Hydrogen Bonding / drug effects
  • Intramolecular Transferases / antagonists & inhibitors
  • Intramolecular Transferases / chemistry*
  • Intramolecular Transferases / metabolism*
  • Ion Channels / chemistry*
  • Ion Channels / metabolism*
  • Models, Molecular
  • Mutant Proteins / chemistry
  • Mutant Proteins / metabolism
  • Protein Structure, Secondary
  • Saccharomyces cerevisiae / drug effects
  • Saccharomyces cerevisiae / enzymology*
  • Squalene / pharmacology
  • Structure-Activity Relationship
  • Substrate Specificity / drug effects
  • Temperature
  • Transformation, Genetic / drug effects
  • Tyrosine / metabolism

Substances

  • Enzyme Inhibitors
  • Ion Channels
  • Mutant Proteins
  • Tyrosine
  • Squalene
  • Intramolecular Transferases
  • lanosterol synthase