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The N···H hydrogen bond strength in the transition state at the limiting step determines the reactivity of cephalosporins in the active site of L1 metallo-β-lactamase

Mariya Grigor'evna Khrenova 1, 2
Mariya Grigor'evna Khrenova
, 
Vladinir Grigor'evich Tsirelson 1, 3
Vladinir Grigor'evich Tsirelson
10.1016/j.mencom.2019.09.004
Published 2019-09-04
Communication , Volume 29, Issue 5, 492-494
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Khrenova M. G., Tsirelson V. G. The N···H hydrogen bond strength in the transition state at the limiting step determines the reactivity of cephalosporins in the active site of L1 metallo-β-lactamase // Mendeleev Communications. 2019. Vol. 29. No. 5. pp. 492-494.
GOST all authors (up to 50) Copy
Khrenova M. G., Tsirelson V. G. The N···H hydrogen bond strength in the transition state at the limiting step determines the reactivity of cephalosporins in the active site of L1 metallo-β-lactamase // Mendeleev Communications. 2019. Vol. 29. No. 5. pp. 492-494.
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TY - JOUR
DO - 10.1016/j.mencom.2019.09.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.004
TI - The N···H hydrogen bond strength in the transition state at the limiting step determines the reactivity of cephalosporins in the active site of L1 metallo-β-lactamase
T2 - Mendeleev Communications
AU - Khrenova, Mariya Grigor'evna
AU - Tsirelson, Vladinir Grigor'evich
PY - 2019
DA - 2019/09/04
PB - Mendeleev Communications
SP - 492-494
IS - 5
VL - 29
ER -
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@article{2019_Khrenova,
author = {Mariya Grigor'evna Khrenova and Vladinir Grigor'evich Tsirelson},
title = {The N···H hydrogen bond strength in the transition state at the limiting step determines the reactivity of cephalosporins in the active site of L1 metallo-β-lactamase},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.004},
number = {5},
pages = {492--494},
doi = {10.1016/j.mencom.2019.09.004}
}
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Khrenova, Mariya Grigor'evna, and Vladinir Grigor'evich Tsirelson. “The N···H hydrogen bond strength in the transition state at the limiting step determines the reactivity of cephalosporins in the active site of L1 metallo-β-lactamase.” Mendeleev Communications, vol. 29, no. 5, Sep. 2019, pp. 492-494. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.004.

Abstract

The combined quantum mechanics/molecular mechanics investigation followed by the detailed electron density analysis for 9 cephalosporin–L1 metallo-β-lactamase complexes revealed correlation between the N···H hydrogen bond strength in the transition state at the limiting step and the reactivity of cephalosporin compounds. The stronger interactions were typical of the less reactive species.

References

1.
QM/MM Methods for Biomolecular Systems
Senn H.M., Thiel W.
Angewandte Chemie - International Edition, 2009
2.
Khrenova M.G., Solovyev I.D., Lapshin G.D., Savitsky A.P.
Mendeleev Communications, 2017
3.
Medvedev M.G., Panova M.V., Chilov G.G., Bushmarinov I.S., Novikov F.N., Stroganov O.V., Zeifman A.A., Svitanko I.V.
Mendeleev Communications, 2017
6.
Modeling the Transient Kinetics of the L1 Metallo-β-Lactamase
Khrenova M.G., Nemukhin A.V.
Journal of Physical Chemistry B, 2018
9.
Overexpression, Purification, and Characterization of the Cloned Metallo-β-Lactamase L1 from Stenotrophomonas maltophilia
Crowder M.W., Walsh T.R., Banovic L., Pettit M., Spencer J.
Antimicrobial Agents and Chemotherapy, 1998
12.
10.1016/j.mencom.2019.09.004_sbref0035b
Hydrogen Bonding – New Insights, 2006
14.
Correlation between electron localization and metal ion mutagenicity in DNA synthesis from QM/MM calculations
Chaudret R., Piquemal J., Andrés Cisneros G.
Physical Chemistry Chemical Physics, 2011
15.
Molecular insight into the interaction mechanisms of amino-2H -imidazole derivatives with BACE1 protease: A QM/MM and QTAIM study
Vega-Hissi E.G., Tosso R., Enriz R.D., Gutierrez L.J.
International Journal of Quantum Chemistry, 2014
16.
Interplay between non-covalent interactions in complexes and crystals with halogen bonds
Bartashevich E.V., Tsirelson V.G.
Russian Chemical Reviews, 2014
21.
10.1016/j.mencom.2019.09.004_sbref0070b
Grin
2014
22.
A simple measure of electron localization in atomic and molecular systems
Becke A.D., Edgecombe K.E.
Journal of Chemical Physics, 1990
23.
Savin A., Becke A.D., Flad J., Nesper R., Preuss H., von Schnering H.G.
1991
24.
Does the topological approach characterize the hydrogen bond?
Fuster F., Silvi B.
Theoretical Chemistry Accounts, 2000
25.
10.1016/j.mencom.2019.09.004_bib0080
Tsirelson
Electron Density and Bonding in Crystals: Principles, Theory and X-ray Diffraction Experiments in Solid State Physics and Chemistry, 1996
26.
An approach to computing electrostatic charges for molecules
Singh U.C., Kollman P.A.
Journal of Computational Chemistry, 1984
27.
Determination of Electrostatic Parameters for a Polarizable Force Field Based on the Classical Drude Oscillator
Anisimov V.M., Lamoureux G., Vorobyov I.V., Huang N., Roux B., MacKerell A.D.
Journal of Chemical Theory and Computation, 2004