title: Tautomerism in computer-aided drug design.
abstract: 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.
authors.affiliation: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology (ETH) Zürich, Zürich, Switzerland. pavel.pospisil@pharma.ethz.ch
authors.forename: Pavel
authors.initials: P
authors.lastname: Pospisil
authors.forename: Patrick
authors.initials: P
authors.lastname: Ballmer
authors.forename: Leonardo
authors.initials: L
authors.lastname: Scapozza
authors.forename: Gerd
authors.initials: G
authors.lastname: Folkers
mesh_terms: D001665:Binding Sites; D003198:Computer Simulation; D019992:Databases as Topic; D015195:Drug Design; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008024:Ligands; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D012984:Software
chemical_list: D008024:Ligands