Structure of HIV-1 protease in complex with potent inhibitor KNI-272 determined by high-resolution X-ray and neutron crystallography

Proc Natl Acad Sci U S A. 2009 Mar 24;106(12):4641-6. doi: 10.1073/pnas.0809400106. Epub 2009 Mar 9.

Abstract

HIV-1 protease is a dimeric aspartic protease that plays an essential role in viral replication. To further understand the catalytic mechanism and inhibitor recognition of HIV-1 protease, we need to determine the locations of key hydrogen atoms in the catalytic aspartates Asp-25 and Asp-125. The structure of HIV-1 protease in complex with transition-state analog KNI-272 was determined by combined neutron crystallography at 1.9-A resolution and X-ray crystallography at 1.4-A resolution. The resulting structural data show that the catalytic residue Asp-25 is protonated and that Asp-125 (the catalytic residue from the corresponding diad-related molecule) is deprotonated. The proton on Asp-25 makes a hydrogen bond with the carbonyl group of the allophenylnorstatine (Apns) group in KNI-272. The deprotonated Asp-125 bonds to the hydroxyl proton of Apns. The results provide direct experimental evidence for proposed aspects of the catalytic mechanism of HIV-1 protease and can therefore contribute substantially to the development of specific inhibitors for therapeutic application.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis
  • Catalytic Domain
  • Crystallography, X-Ray
  • HIV Protease / chemistry*
  • HIV Protease / metabolism
  • HIV Protease Inhibitors / chemistry*
  • HIV Protease Inhibitors / metabolism
  • Hydrogen Bonding
  • Models, Molecular
  • Neutron Diffraction*
  • Oligopeptides / chemistry*
  • Oligopeptides / metabolism
  • Protein Structure, Tertiary
  • Static Electricity
  • Water / chemistry

Substances

  • HIV Protease Inhibitors
  • Oligopeptides
  • Water
  • HIV Protease
  • p16 protease, Human immunodeficiency virus 1
  • kynostatin 272

Associated data

  • PDB/2ZYE
  • PDB/3FX5