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Title: Quantum Mechanical Energy-based Screening of Combinatorially Generated Library of Tautomers. TauTGen. A Tautomer Generator Program

Abstract

Many computational methods have been derived from quantum mechanics for molecular and extended systems. We advocate that these methods will soon become indispensable research tools of combinatorial chemistry. Although applications of these combinatorial methods driven by quantum-mechanics-derived computational engines seem to be distant, our recent experience suggests the opposite. We developed algorithms and codes to search for the most stable tautomers of molecules. In our approach, we: (i) create large libraries of molecular tautomers using combinatorial methods, and (ii) prescreen these libraries using quantum chemical electronic structure methods. We have identified many adiabatically bound and previously unknown tautomers of anionic nucleic acid bases. Our results unraveled that ordering of nucleic acid bases according to their affinity to an excess electron is: G > U > T > C > A , when all biologically relevant tautomers are considered. Acknowledgements This work was supported by the: (i) US DOE Office of Biological and Environmental Research, Low Dose Radiation Research Program (M.G.) and (ii) Polish State Committee for Scientific Research (KBN) Grant DS/8221-4-0140-4 (M.H.). M.H. thanks for financial support from the European Union Social Funds ZPORR/2.22/II/2.6/ARP/U/2/O5. M.H. is a holder of the award from the Fundation for Polish Science (FNP). R.A.B. acknowledgesmore » the financial support from Nanoquant EC Marie Curie Research Training Network, contract number: MRTN-506842. Computing resources were available through: (i) the Academic Computer Center in Gdansk (TASK) (ii) a Computational Grand Challenge Application grant from the Molecular Sciences Computing Facility (MSCF) in the Environmental Molecular Sciences Laboratory located at the Pacific Northwest National Laboratory, and (iii) the National Energy Research Scientific Computing Center (NERSC). The MSCF is funded by DOE’s Office of Biological and Environmental Research. PNNL is operated by Battelle for the U.S. DOE under Contract DE-AC06-76RLO 1830.« less

Authors:
;
Publication Date:
Research Org.:
Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)
Sponsoring Org.:
USDOE
OSTI Identifier:
902951
Report Number(s):
PNNL-SA-50679
3565; KC0302010; TRN: US200719%%85
DOE Contract Number:
AC05-76RL01830
Resource Type:
Journal Article
Resource Relation:
Journal Name: Journal of Chemical Information and Modeling, 47(2):686-694; Journal Volume: 47; Journal Issue: 2
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; ALGORITHMS; ELECTRONIC STRUCTURE; NUCLEIC ACIDS; QUANTUM MECHANICS; ISOMERS; Environmental Molecular Sciences Laboratory

Citation Formats

Haranczyk, Maciej, and Gutowski, Maciej S. Quantum Mechanical Energy-based Screening of Combinatorially Generated Library of Tautomers. TauTGen. A Tautomer Generator Program. United States: N. p., 2007. Web. doi:10.1021/ci6002703.
Haranczyk, Maciej, & Gutowski, Maciej S. Quantum Mechanical Energy-based Screening of Combinatorially Generated Library of Tautomers. TauTGen. A Tautomer Generator Program. United States. doi:10.1021/ci6002703.
Haranczyk, Maciej, and Gutowski, Maciej S. Thu . "Quantum Mechanical Energy-based Screening of Combinatorially Generated Library of Tautomers. TauTGen. A Tautomer Generator Program". United States. doi:10.1021/ci6002703.
@article{osti_902951,
title = {Quantum Mechanical Energy-based Screening of Combinatorially Generated Library of Tautomers. TauTGen. A Tautomer Generator Program},
author = {Haranczyk, Maciej and Gutowski, Maciej S},
abstractNote = {Many computational methods have been derived from quantum mechanics for molecular and extended systems. We advocate that these methods will soon become indispensable research tools of combinatorial chemistry. Although applications of these combinatorial methods driven by quantum-mechanics-derived computational engines seem to be distant, our recent experience suggests the opposite. We developed algorithms and codes to search for the most stable tautomers of molecules. In our approach, we: (i) create large libraries of molecular tautomers using combinatorial methods, and (ii) prescreen these libraries using quantum chemical electronic structure methods. We have identified many adiabatically bound and previously unknown tautomers of anionic nucleic acid bases. Our results unraveled that ordering of nucleic acid bases according to their affinity to an excess electron is: G > U > T > C > A , when all biologically relevant tautomers are considered. Acknowledgements This work was supported by the: (i) US DOE Office of Biological and Environmental Research, Low Dose Radiation Research Program (M.G.) and (ii) Polish State Committee for Scientific Research (KBN) Grant DS/8221-4-0140-4 (M.H.). M.H. thanks for financial support from the European Union Social Funds ZPORR/2.22/II/2.6/ARP/U/2/O5. M.H. is a holder of the award from the Fundation for Polish Science (FNP). R.A.B. acknowledges the financial support from Nanoquant EC Marie Curie Research Training Network, contract number: MRTN-506842. Computing resources were available through: (i) the Academic Computer Center in Gdansk (TASK) (ii) a Computational Grand Challenge Application grant from the Molecular Sciences Computing Facility (MSCF) in the Environmental Molecular Sciences Laboratory located at the Pacific Northwest National Laboratory, and (iii) the National Energy Research Scientific Computing Center (NERSC). The MSCF is funded by DOE’s Office of Biological and Environmental Research. PNNL is operated by Battelle for the U.S. DOE under Contract DE-AC06-76RLO 1830.},
doi = {10.1021/ci6002703},
journal = {Journal of Chemical Information and Modeling, 47(2):686-694},
number = 2,
volume = 47,
place = {United States},
year = {Thu Mar 01 00:00:00 EST 2007},
month = {Thu Mar 01 00:00:00 EST 2007}
}