Quantum mechanical energy-based screening of combinatorially generated library of tautomers. TauTGen: a tautomer generator program.
We describe a procedure of finding low-energy tautomers of a molecule. The procedure consists of (i) combinatorial generation of a library of tautomers, (ii) screening based on the results of geometry optimization of initial structures performed at the density functional level of theory, and (iii) final refinement of geometry for the top hits at the second-order Möller-Plesset level of theory followed by single-point energy calculations at the coupled cluster level of theory with single, double, and perturbative triple excitations. The library of initial structures of various tautomers is generated with TauTGen, a tautomer generator program. The procedure proved to be successful for these molecular systems for which common chemical knowledge had not been sufficient to predict the most stable structures.
Harańczyk
Maciej
M
Department of Chemistry, University of Gdańsk, 80-952 Gdańsk, Poland.
Gutowski
Maciej
M
D000838:Anions / Q000737:chemistry; D002412:Cations / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003545:Cysteine / Q000737:chemistry; D004353:Drug Evaluation, Preclinical / Q000379:methods*; D006859:Hydrogen / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011685:Purine Nucleotides / Q000737:chemistry; D011789:Quantum Theory; D012984:Software; D014498:Uracil / Q000737:chemistry
D000838:Anions; D002412:Cations; D011685:Purine Nucleotides; D014498:Uracil; D006859:Hydrogen; D003545:Cysteine