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Journal article

Tautomerism in computer-aided drug design.

  • Pospisil P Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH) Zürich, Zürich, Switzerland. pavel.pospisil@pharma.ethz.ch
  • Ballmer P
  • Scapozza L
  • Folkers G
  • 2004-02-03
Published in:
  • Journal of receptor and signal transduction research. - 2003
Binding Sites
Computer Simulation
Databases as Topic
Drug Design
Hydrogen Bonding
Hydrogen-Ion Concentration
Kinetics
Ligands
Models, Chemical
Models, Molecular
Molecular Conformation
Software
English Tautomers are often disregarded in computer-aided molecular modeling applications. Little is known about the different tautomeric states of a molecule and they are rarely registered in chemical databases. Tautomeric forms of a molecule differ in shape, functional groups, surface, and hydrogen-bonding pattern. Calculation of physical-chemical properties and molecular descriptors differ from one tautomeric state to the other as it is demonstrated with an example of the log P calculation, similarity index, and the complementarity pattern to the targeted protein. Considering tautomery in ligand-protein interactions therefore has a significant impact on the prediction of the ligand binding using various docking techniques. This article points on hitherto unaddressed issue of tautomerism in computer-aided drug design.
Language
  • English
Open access status
green
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Persistent URL
https://sonar.ch/global/documents/67059
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