Low‐Barrier and Canonical Hydrogen Bonds Modulate Activity and Specificity of a Catalytic Triad
- Authors:
-
- Graduate School of Genome Science and Technology University of Tennessee Knoxville TN 37996 USA, Present address: Department of Pharmacological Sciences Icahn School of Medicine at Mount Sinai New York NY 10029 USA
- Department of Biochemistry and Cellular and Molecular Biology University of Tennessee Knoxville TN 37996 USA
- Molecular Interaction Analysis Shared Resource St. Jude Children's Research Hospital Memphis TN 38105 USA
- Department of Structural Biology St. Jude Children's Research Hospital Memphis TN 38105 USA
- Department of Biochemistry and Cellular and Molecular Biology University of Tennessee Knoxville TN 37996 USA, National Science Foundation Alexandria VA 22314 USA
- Department of Structural Biology St. Jude Children's Research Hospital Memphis TN 38105 USA, Oak Ridge National Laboratory Oak Ridge TN 37830 USA
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1566163
- Grant/Contract Number:
- FWP ERKP291
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Angewandte Chemie
- Additional Journal Information:
- Journal Name: Angewandte Chemie Journal Volume: 131 Journal Issue: 45; Journal ID: ISSN 0044-8249
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Kumar, Prashasti, Agarwal, Pratul K., Waddell, M. Brett, Mittag, Tanja, Serpersu, Engin H., and Cuneo, Matthew J. Low‐Barrier and Canonical Hydrogen Bonds Modulate Activity and Specificity of a Catalytic Triad. Germany: N. p., 2019.
Web. doi:10.1002/ange.201908535.
Kumar, Prashasti, Agarwal, Pratul K., Waddell, M. Brett, Mittag, Tanja, Serpersu, Engin H., & Cuneo, Matthew J. Low‐Barrier and Canonical Hydrogen Bonds Modulate Activity and Specificity of a Catalytic Triad. Germany. https://doi.org/10.1002/ange.201908535
Kumar, Prashasti, Agarwal, Pratul K., Waddell, M. Brett, Mittag, Tanja, Serpersu, Engin H., and Cuneo, Matthew J. Tue .
"Low‐Barrier and Canonical Hydrogen Bonds Modulate Activity and Specificity of a Catalytic Triad". Germany. https://doi.org/10.1002/ange.201908535.
@article{osti_1566163,
title = {Low‐Barrier and Canonical Hydrogen Bonds Modulate Activity and Specificity of a Catalytic Triad},
author = {Kumar, Prashasti and Agarwal, Pratul K. and Waddell, M. Brett and Mittag, Tanja and Serpersu, Engin H. and Cuneo, Matthew J.},
abstractNote = {},
doi = {10.1002/ange.201908535},
journal = {Angewandte Chemie},
number = 45,
volume = 131,
place = {Germany},
year = {2019},
month = {9}
}
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1002/ange.201908535
https://doi.org/10.1002/ange.201908535
Other availability
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Subangstrom Crystallography Reveals that Short Ionic Hydrogen Bonds, and Not a His-Asp Low-Barrier Hydrogen Bond, Stabilize the Transition State in Serine Protease Catalysis
journal, July 2006
- Fuhrmann, Cynthia N.; Daugherty, Matthew D.; Agard, David A.
- Journal of the American Chemical Society, Vol. 128, Issue 28
Electrostatic Interactions Guide the Active Site Face of a Structure-Specific Ribonuclease to Its RNA Substrate †
journal, August 2008
- Plantinga, Matthew J.; Korennykh, Alexei V.; Piccirilli, Joseph A.
- Biochemistry, Vol. 47, Issue 34
Structural Basis of Perturbed pKa Values of Catalytic Groups in Enzyme Active Sites
journal, February 2002
- Harris, Thomas K.; Turner, George J.
- IUBMB Life (International Union of Biochemistry and Molecular Biology: Life), Vol. 53, Issue 2
An explanation for rapid enzyme-catalyzed proton abstraction from carbon acids: importance of late transition states in concerted mechanisms
journal, December 1993
- Gerlt, John A.; Gassman, Paul G.
- Journal of the American Chemical Society, Vol. 115, Issue 24
Plasticity of enzyme active sites
journal, August 2002
- Todd, Annabel E.; Orengo, Christine A.; Thornton, Janet M.
- Trends in Biochemical Sciences, Vol. 27, Issue 8
Short strong hydrogen bonds: can they explain enzymic catalysis?
journal, March 1996
- Peter Guthrie, J.
- Chemistry & Biology, Vol. 3, Issue 3
Protonation-State Dependence of Hydrogen Bond Strengths and Exchange Rates in a Serine Protease Catalytic Triad: Bovine Chymotrypsinogen A †
journal, January 1996
- Markley, John L.; Westler, William M.
- Biochemistry, Vol. 35, Issue 34
Ladungen verschieben Protonierungen: Neutronenbeugung zeigt, dass Anilin und 2-Aminopyridin protoniert an Trypsin binden
journal, March 2017
- Schiebel, Johannes; Gaspari, Roberto; Sandner, Anna
- Angewandte Chemie, Vol. 129, Issue 17
Encoding of Promiscuity in an Aminoglycoside Acetyltransferase
journal, October 2018
- Kumar, Prashasti; Selvaraj, Brinda; Serpersu, Engin H.
- Journal of Medicinal Chemistry, Vol. 61, Issue 22
A low-barrier hydrogen bond mediates antibiotic resistance in a noncanonical catalytic triad
journal, April 2018
- Kumar, Prashasti; Serpersu, Engin H.; Cuneo, Matthew J.
- Science Advances, Vol. 4, Issue 4
Aminoglycoside 2′-N-acetyltransferase from Mycobacterium tuberculosis in complex with coenzyme A and aminoglycoside substrates
journal, August 2002
- Vetting, Matthew W.; Hegde, Subray S.; Javid-Majd, Farah
- Nature Structural Biology, Vol. 9, Issue 9
Protein Dynamics Are Influenced by the Order of Ligand Binding to an Antibiotic Resistance Enzyme
journal, December 2013
- Norris, Adrianne L.; Nickels, Jonathan; Sokolov, Alexei P.
- Biochemistry, Vol. 53, Issue 1
BIOCHEMISTRY: How Enzymes Work
journal, June 2008
- Ringe, D.; Petsko, G. A.
- Science, Vol. 320, Issue 5882
A low-barrier hydrogen bond in the catalytic triad of serine proteases
journal, June 1994
- Frey, P.; Whitt, S.; Tobin, J.
- Science, Vol. 264, Issue 5167
The Low Barrier Hydrogen Bond in Enzymatic Catalysis
journal, October 1998
- Cleland, W. Wallace; Frey, Perry A.; Gerlt, John A.
- Journal of Biological Chemistry, Vol. 273, Issue 40
Interactions of Coenzyme A with the Aminoglycoside Acetyltransferase (3)-IIIb and Thermodynamics of a Ternary System
journal, May 2010
- Norris, Adrianne L.; Serpersu, Engin H.
- Biochemistry, Vol. 49, Issue 19
X-ray Snapshot of HIV-1 Protease in Action: Observation of Tetrahedral Intermediate and Short Ionic Hydrogen Bond SIHB with Catalytic Aspartate
journal, May 2010
- Das, Amit; Mahale, Smita; Prashar, Vishal
- Journal of the American Chemical Society, Vol. 132, Issue 18
Hydrogen Bonding at the Active Site of Δ 5 -3-Ketosteroid Isomerase †
journal, December 1997
- Zhao, Qinjian; Abeygunawardana, Chitrananda; Gittis, Apostolos G.
- Biochemistry, Vol. 36, Issue 48
Ligand promiscuity through the eyes of the aminoglycoside N 3 acetyltransferase IIa : Molecular Basis of Ligand Promiscuity
journal, June 2013
- Norris, Adrianne L.; Serpersu, Engin H.
- Protein Science, Vol. 22, Issue 7
Direct evidence that an extended hydrogen-bonding network influences activation of pyridoxal 5′-phosphate in aspartate aminotransferase
journal, February 2017
- Dajnowicz, Steven; Parks, Jerry M.; Hu, Xiche
- Journal of Biological Chemistry, Vol. 292, Issue 14
Low-barrier hydrogen bonds and enzymic catalysis
journal, June 1994
- Cleland, W.; Kreevoy, M.
- Science, Vol. 264, Issue 5167
The low barrier hydrogen bond (LBHB) proposal revisited: The case of the Asp ··· His pair in serine proteases
journal, April 2004
- Schutz, Claudia N.; Warshel, Arieh
- Proteins: Structure, Function, and Bioinformatics, Vol. 55, Issue 3
Thermodynamics of an aminoglycoside modifying enzyme with low substrate promiscuity: The aminoglycoside N3 acetyltransferase-VIa : Thermodynamic Basis of Ligand Promiscuity
journal, March 2017
- Kumar, Prashasti; Serpersu, Engin H.
- Proteins: Structure, Function, and Bioinformatics, Vol. 85, Issue 7
Thermodynamics and Kinetics of Association of Antibiotics with the Aminoglycoside Acetyltransferase (3)-IIIb, a Resistance-Causing Enzyme
journal, May 2010
- Norris, Adrianne L.; Özen, Can; Serpersu, Engin H.
- Biochemistry, Vol. 49, Issue 19
Charges Shift Protonation: Neutron Diffraction Reveals that Aniline and 2-Aminopyridine Become Protonated Upon Binding to Trypsin
journal, March 2017
- Schiebel, Johannes; Gaspari, Roberto; Sandner, Anna
- Angewandte Chemie International Edition, Vol. 56, Issue 17
Thermodynamics of Aminoglycoside Binding to Aminoglycoside-3‘-phosphotransferase IIIa Studied by Isothermal Titration Calorimetry †
journal, November 2004
- Özen, Can; Serpersu, Engin H.
- Biochemistry, Vol. 43, Issue 46
Long-range Electrostatic Complementarity Governs Substrate Recognition by Human Chymotrypsin C, a Key Regulator of Digestive Enzyme Activation
journal, February 2013
- Batra, Jyotica; Szabó, András; Caulfield, Thomas R.
- Journal of Biological Chemistry, Vol. 288, Issue 14
Combined High-Resolution Neutron and X-ray Analysis of Inhibited Elastase Confirms the Active-Site Oxyanion Hole but Rules against a Low-Barrier Hydrogen Bond
journal, August 2009
- Tamada, Taro; Kinoshita, Takayoshi; Kurihara, Kazuo
- Journal of the American Chemical Society, Vol. 131, Issue 31
Electrostatic Origin of the Catalytic Power of Enzymes and the Role of Preorganized Active Sites
journal, October 1998
- Warshel, Arieh
- Journal of Biological Chemistry, Vol. 273, Issue 42
Solid State NMR Studies of Hydrogen Bonding in a Citrate Synthase Inhibitor Complex †
journal, June 1999
- Gu, Zhengtian; Drueckhammer, Dale G.; Kurz, Linda
- Biochemistry, Vol. 38, Issue 25
Probing Electrostatic Interactions along the Reaction Pathway of a Glycoside Hydrolase: Histidine Characterization by NMR Spectroscopy †
journal, June 2007
- Schubert, Mario; Poon, David K. Y.; Wicki, Jacqueline
- Biochemistry, Vol. 46, Issue 25
On low-barrier hydrogen bonds and enzyme catalysis
journal, July 1995
- Warshel, A.; Papazyan, A.; Kollman, P.
- Science, Vol. 269, Issue 5220