Abstract
We describe a method for the systematic improvement of reaction coordinates in quantum mechanical/molecular mechanical (QM/MM) calculations of reaction free-energy profiles. In umbrella-sampling free-energy calculations, a biasing potential acting on a chosen reaction coordinate is used to sample the system in reactant, product, and transition states. Sharp, nearly discontinuous changes along the resulting reaction path are used to identify coordinates that are relevant for the reaction but not properly sampled. These degrees of freedom are then included in an extended reaction coordinate. The general formalism is illustrated for the catalytic cleavage of the RNA backbone of an RNA/DNA hybrid duplex by the RNase H enzyme of Bacillus halodurans. We find that in the initial attack of the phosphate diester by water, the oxygen-phosphorus distances alone are not sufficient as reaction coordinates, resulting in substantial hysteresis in the proton degrees of freedom and a barrier that is too low (approximately 10 kcal/mol). If the proton degrees of freedom are included in an extended reaction coordinate, we obtain a barrier of 21.6 kcal/mol consistent with the experimental rates. As the barrier is approached, the attacking water molecule transfers one of its protons to the O1P oxygen of the phosphate group. At the barrier top, the resulting hydroxide ion forms a penta-coordinated phosphate intermediate. The method used to identify important degrees of freedom, and the procedure to optimize the reaction coordinate are general and should be useful both in classical and in QM/MM free-energy calculations.
MeSH Terms
Bacillus/enzymology
Biocatalysis
Computer Simulation
DNA, Bacterial/chemistry,metabolism
Models, Molecular
Protein Binding
Protein Conformation
Quantum Theory
RNA, Bacterial/chemistry,metabolism
Ribonuclease H/chemistry,metabolism
Thermodynamics
Chemicals
DNA, Bacterial
RNA, Bacterial
Ribonuclease H
Authors & Affiliations
4 authors, click to expand affiliations / ORCID
Rosta Edina
Laboratory of Chemical Physics, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892-0520, USA.
Woodcock H Lee
Brooks Bernard R
Hummer Gerhard
References (26)
26 references, click to expand
-
Towards accurate ab initio QM/MM calculations of free-energy profiles of enzymatic reactions.
J Phys Chem B. 2006 Feb 16;110(6):2934-41
PMID: 16471904
-
The coupling of structural fluctuations to hydride transfer in dihydrofolate reductase.
Proteins. 2004 Nov 15;57(3):444-57
PMID: 15382243
-
Mapping the transition state for ATP hydrolysis: implications for enzymatic catalysis.
Chem Biol. 1995 Nov;2(11):729-39
PMID: 9383480
-
Models for biological phosphoryl transfer.
Biochim Biophys Acta. 2004 Mar 11;1697(1-2):279-87
PMID: 15023368
-
Catalytic mechanism of human DNA polymerase lambda with Mg2+ and Mn2+ from ab initio quantum mechanical/molecular mechanical studies.
DNA Repair (Amst). 2008 Nov 1;7(11):1824-34
PMID: 18692600
-
Random walk in orthogonal space to achieve efficient free-energy simulation of complex systems.
Proc Natl Acad Sci U S A. 2008 Dec 23;105(51):20227-32
PMID: 19075242
-
Human RNase H1 uses one tryptophan and two lysines to position the enzyme at the 3'-DNA/5'-RNA terminus of the heteroduplex substrate.
J Biol Chem. 2003 Dec 12;278(50):49860-7
PMID: 14506260
-
On the mechanism of hydrolysis of phosphate monoesters dianions in solutions and proteins.
J Am Chem Soc. 2006 Nov 29;128(47):15310-23
PMID: 17117884
-
Phosphodiester cleavage in ribonuclease H occurs via an associative two-metal-aided catalytic mechanism.
J Am Chem Soc. 2008 Aug 20;130(33):10955-62
PMID: 18662000
-
The role of metal ions in phosphate ester hydrolysis.
Org Biomol Chem. 2007 Jul 7;5(13):2098-108
PMID: 17581653
-
Type II restriction endonucleases: structure and mechanism.
Cell Mol Life Sci. 2005 Mar;62(6):685-707
PMID: 15770420
-
Making and breaking nucleic acids: two-Mg2+-ion catalysis and substrate specificity.
Mol Cell. 2006 Apr 7;22(1):5-13
PMID: 16600865
-
A general two-metal-ion mechanism for catalytic RNA.
Proc Natl Acad Sci U S A. 1993 Jul 15;90(14):6498-502
PMID: 8341661
-
A recipe for the computation of the free energy barrier and the lowest free energy path of concerted reactions.
J Phys Chem B. 2005 Apr 14;109(14):6676-87
PMID: 16851750
-
Exploring SCC-DFTB paths for mapping QM/MM reaction mechanisms.
J Phys Chem A. 2007 Jul 5;111(26):5720-8
PMID: 17555303
-
A water-mediated and substrate-assisted catalytic mechanism for Sulfolobus solfataricus DNA polymerase IV.
J Am Chem Soc. 2007 Apr 18;129(15):4731-7
PMID: 17375926
-
Alkaline phosphatase mono- and diesterase reactions: comparative transition state analysis.
J Am Chem Soc. 2006 Feb 1;128(4):1293-303
PMID: 16433548
-
Escaping free-energy minima.
Proc Natl Acad Sci U S A. 2002 Oct 1;99(20):12562-6
PMID: 12271136
-
Reactivity of alcohols toward the phosphoenzyme intermediate in the protein-tyrosine phosphatase-catalyzed reaction: probing the transition state of the dephosphorylation step.
Biochemistry. 1996 Sep 10;35(36):11797-804
PMID: 8794761
-
On the interpretation of the observed linear free energy relationship in phosphate hydrolysis: a thorough computational study of phosphate diester hydrolysis in solution.
Biochemistry. 2008 Mar 25;47(12):3725-35
PMID: 18307312
-
Interfacing Q-Chem and CHARMM to perform QM/MM reaction path calculations.
J Comput Chem. 2007 Jul 15;28(9):1485-1502
PMID: 17334987
-
On possible pitfalls in ab initio quantum mechanics/molecular mechanics minimization approaches for studies of enzymatic reactions.
J Phys Chem B. 2005 Aug 18;109(32):15645-50
PMID: 16852982
-
Crystal structures of RNase H bound to an RNA/DNA hybrid: substrate specificity and metal-dependent catalysis.
Cell. 2005 Jul 1;121(7):1005-16
PMID: 15989951
-
Advances in methods and algorithms in a modern quantum chemistry program package.
Phys Chem Chem Phys. 2006 Jul 21;8(27):3172-91
PMID: 16902710
-
Structure of human RNase H1 complexed with an RNA/DNA hybrid: insight into HIV reverse transcription.
Mol Cell. 2007 Oct 26;28(2):264-76
PMID: 17964265
-
Local elevation: a method for improving the searching properties of molecular dynamics simulation.
J Comput Aided Mol Des. 1994 Dec;8(6):695-708
PMID: 7738605