Horse Liver Alcohol Dehydrogenase: Zinc Coordination and Catalysis
Abstract
During catalysis by liver alcohol dehydrogenase (ADH), a water bound to the catalytic zinc is replaced by the oxygen of the substrates. The mechanism might involve a pentacoordinated zinc or a double-displacement reaction with participation by a nearby glutamate residue, as suggested by studies of human ADH3, yeast ADH1, and some other tetrameric ADHs. Zinc coordination and participation of water in the enzyme mechanism were investigated by X-ray crystallography. The apoenzyme and its complex with adenosine 5'-diphosphoribose have an open protein conformation with the catalytic zinc in one position, tetracoordinated by Cys-46, His-67, Cys-174, and a water molecule. The bidentate chelators 2,2'-bipyridine and 1,10-phenanthroline displace the water and form a pentacoordinated zinc. The enzyme–NADH complex has a closed conformation similar to that of ternary complexes with coenzyme and substrate analogues; the coordination of the catalytic zinc is similar to that found in the apoenzyme, except that a minor, alternative position for the catalytic zinc is ~1.3 Å from the major position and closer to Glu-68, which could form the alternative coordination to the catalytic zinc. Complexes with NADH and N-1-methylhexylformamide or N-benzylformamide (or with NAD+ and fluoro alcohols) have the classical tetracoordinated zinc, and no water is bound to themore »
- Authors:
-
- Univ. of Iowa, Iowa City, IA (United States)
- Univ. of Iowa, Iowa City, IA (United States); Southern Illinois Univ. School of Medicine, Springfield, IL (United States)
- Univ. of Iowa, Iowa City, IA (United States); Kemin Industries, Des Moines, IA (United States)
- Univ. of Iowa, Iowa City, IA (United States); Vanderbilt University of Visual Sciences, Nashville, TN (United States)
- Univ. of Iowa, Iowa City, IA (United States); Institute for Stem Cell Biology and Regenerative Medicine (inSTEM), Bangalore (India)
- Publication Date:
- Research Org.:
- Argonne National Laboratory (ANL), Argonne, IL (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities Division; National Institutes of Health (NIH)
- OSTI Identifier:
- 1375359
- Grant/Contract Number:
- AC02-06CH11357; AA00279
- Resource Type:
- Journal Article: Accepted Manuscript
- Journal Name:
- Biochemistry
- Additional Journal Information:
- Journal Volume: 56; Journal Issue: 28; Journal ID: ISSN 0006-2960
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- ENGLISH
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES; zinc; alcohols; peptides and proteins; chemical structure; nicotinamide
Citation Formats
Plapp, Bryce V., Savarimuthu, Baskar Raj, Ferraro, Daniel J., Rubach, Jon K., Brown, Eric N., and Ramaswamy, S. Horse Liver Alcohol Dehydrogenase: Zinc Coordination and Catalysis. United States: N. p., 2017.
Web. doi:10.1021/acs.biochem.7b00446.
Plapp, Bryce V., Savarimuthu, Baskar Raj, Ferraro, Daniel J., Rubach, Jon K., Brown, Eric N., & Ramaswamy, S. Horse Liver Alcohol Dehydrogenase: Zinc Coordination and Catalysis. United States. https://doi.org/10.1021/acs.biochem.7b00446
Plapp, Bryce V., Savarimuthu, Baskar Raj, Ferraro, Daniel J., Rubach, Jon K., Brown, Eric N., and Ramaswamy, S. 2017.
"Horse Liver Alcohol Dehydrogenase: Zinc Coordination and Catalysis". United States. https://doi.org/10.1021/acs.biochem.7b00446. https://www.osti.gov/servlets/purl/1375359.
@article{osti_1375359,
title = {Horse Liver Alcohol Dehydrogenase: Zinc Coordination and Catalysis},
author = {Plapp, Bryce V. and Savarimuthu, Baskar Raj and Ferraro, Daniel J. and Rubach, Jon K. and Brown, Eric N. and Ramaswamy, S.},
abstractNote = {During catalysis by liver alcohol dehydrogenase (ADH), a water bound to the catalytic zinc is replaced by the oxygen of the substrates. The mechanism might involve a pentacoordinated zinc or a double-displacement reaction with participation by a nearby glutamate residue, as suggested by studies of human ADH3, yeast ADH1, and some other tetrameric ADHs. Zinc coordination and participation of water in the enzyme mechanism were investigated by X-ray crystallography. The apoenzyme and its complex with adenosine 5'-diphosphoribose have an open protein conformation with the catalytic zinc in one position, tetracoordinated by Cys-46, His-67, Cys-174, and a water molecule. The bidentate chelators 2,2'-bipyridine and 1,10-phenanthroline displace the water and form a pentacoordinated zinc. The enzyme–NADH complex has a closed conformation similar to that of ternary complexes with coenzyme and substrate analogues; the coordination of the catalytic zinc is similar to that found in the apoenzyme, except that a minor, alternative position for the catalytic zinc is ~1.3 Å from the major position and closer to Glu-68, which could form the alternative coordination to the catalytic zinc. Complexes with NADH and N-1-methylhexylformamide or N-benzylformamide (or with NAD+ and fluoro alcohols) have the classical tetracoordinated zinc, and no water is bound to the zinc or the nicotinamide rings. Here, the major forms of the enzyme in the mechanism have a tetracoordinated zinc, where the carboxylate group of Glu-68 could participate in the exchange of water and substrates on the zinc. Hydride transfer in the Michaelis complexes does not involve a nearby water.},
doi = {10.1021/acs.biochem.7b00446},
url = {https://www.osti.gov/biblio/1375359},
journal = {Biochemistry},
issn = {0006-2960},
number = 28,
volume = 56,
place = {United States},
year = {Thu Jun 22 00:00:00 EDT 2017},
month = {Thu Jun 22 00:00:00 EDT 2017}
}
Web of Science
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Works referencing / citing this record:
Peroxidase activity of new mixed‐valence cobalt complexes with ligands derived from pyridoxal
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- Fontana, Liniquer André; Siqueira, Josiéli Demetrio; Ceolin, Joice
- Applied Organometallic Chemistry, Vol. 33, Issue 7