Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Adapting to oxygen: 3-Hydroxyanthrinilate 3,4-dioxygenase employs loop dynamics to accommodate two substrates with disparate polarities

Journal Article · · Journal of Biological Chemistry
 [1];  [2];  [1]
  1. Univ. of Texas at San Antonio, TX (United States). Dept. of Chemistry
  2. Univ. of Pennsylvania, Philadelphia, PA (United States). Dept. of Biochemistry and Biophysics. Perelman School of Medicine

3-Hydroxyanthranilate 3,4-dioxygenase (HAO) is an iron-dependent protein that activates O2 and inserts both oxygen atoms into 3-hydroxyanthranilate (3-HAA). An intriguing question is how HAO can rapidly bind O2, even though local O2 concentrations and diffusion rates are relatively low. Here, a close inspection of the HAO structures revealed that substrate- and inhibitor-bound structures exhibit a closed conformation with three hydrophobic loop regions moving toward the catalytic iron center, whereas the ligand-free structure is open. We hypothesized that these loop movements enhance O2 binding to the binary complex of HAO and 3-HAA. We found that the carboxyl end of 3-HAA triggers changes in two loop regions and that the third loop movement appears to be driven by an H-bond interaction between Asn27 and Ile142. Mutational analyses revealed that N27A, I142A, and I142P variants cannot form a closed conformation, and steady-state kinetic assays indicated that these variants have a substantially higher Km for O2 than WT HAO. This observation suggested enhanced hydrophobicity at the iron center resulting from the concerted loop movements after the binding of the primary substrate, which is hydrophilic. Given that O2 is nonpolar, the increased hydrophobicity at the iron center of the binary complex appears to be essential for rapid O2 binding and activation, explaining the reason for the 3-HAA–induced loop movements. Because substrate binding-induced open-to-closed conformational changes are common, the results reported here may help further our understanding of how oxygen is enriched in nonheme iron-dependent dioxygenases.

Research Organization:
Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
AC02-06CH11357; AC02-76SF00515
OSTI ID:
1815038
Alternate ID(s):
OSTI ID: 1463716
Journal Information:
Journal of Biological Chemistry, Journal Name: Journal of Biological Chemistry Journal Issue: 27 Vol. 293; ISSN 0021-9258
Publisher:
American Society for Biochemistry and Molecular BiologyCopyright Statement
Country of Publication:
United States
Language:
ENGLISH

References (38)

An X-ray study of azide methaemoglobin journal October 1966
The kynurenine pathway of tryptophan degradation as a drug target journal February 2004
Versatility of biological non-heme Fe(II) centers in oxygen activation reactions journal February 2008
Endogenous kynurenines as targets for drug discovery and development journal August 2002
Kynurenines in the mammalian brain: when physiology meets pathology journal June 2012
Anaerobic enzyme*substrate structures provide insight into the reaction mechanism of the copper-dependent quercetin 2,3-dioxygenase journal December 2002
Deciphering key features in protein structures with the new ENDscript server journal April 2014
Linking Crystallographic Model and Data Quality journal May 2012
Tryptophan Catabolism: Identification and Characterization of a New Degradative Pathway journal November 2005
O2 Migration Pathways Are Not Conserved across Proteins of a Similar Fold journal November 2007
Crystal structure of bovine 3-hydroxyanthranilate 3,4-dioxygenase: Crystal Structure of B3HAO journal February 2009
Finding Intermediates in the O2 Activation Pathways of Non-Heme Iron Oxygenases journal October 2007
NMRPipe: A multidimensional spectral processing system based on UNIX pipes journal November 1995
Order of substrate binding in bacterial phenylalanine hydroxylase and its mechanistic implication for pterin-dependent oxygenases journal January 2003
Exploring the gas access routes in a [NiFeSe] hydrogenase using crystals pressurized with krypton and oxygen journal August 2020
An X-ray study of azide methaemoglobin journal October 1966
[20] Processing of X-ray diffraction data collected in oscillation mode book January 1997
NAD Biosynthesis journal December 2003
Finding Intermediates in the O 2 Activation Pathways of Non-Heme Iron Oxygenases journal July 2007
Substrate-Induced Conformational Changes in Escherichia coli Taurine/α-Ketoglutarate Dioxygenase and Insight into the Oligomeric Structure journal May 2003
The Mechanism of Inactivation of 3-Hydroxyanthranilate-3,4-dioxygenase by 4-Chloro-3-hydroxyanthranilate journal May 2005
Structural Studies on 3-Hydroxyanthranilate-3,4-dioxygenase:  The Catalytic Mechanism of a Complex Oxidation Involved in NAD Biosynthesis , journal May 2005
Cryo-EM structure of the respiratory syncytial virus RNA polymerase journal January 2020
Cavin1 intrinsically disordered domains are essential for fuzzy electrostatic interactions and caveola formation journal February 2021
Multi-functionality of a tryptophan residue conserved in substrate-binding groove of GH19 chitinases journal January 2021
Conformational switch triggered by  -ketoglutarate in a halogenase of curacin A biosynthesis journal July 2010
Crystal Structure and Functional Analysis of the Extradiol Dioxygenase LapB from a Long-chain Alkylphenol Degradation Pathway in Pseudomonas journal October 2009
Hydrophobic Effect Drives Oxygen Uptake in Myoglobin via Histidine E7 journal January 2013
An Iron Reservoir to the Catalytic Metal: THE RUBREDOXIN IRON IN AN EXTRADIOL DIOXYGENASE journal April 2015
Equality of the in vivo and in Vitro Oxygen-Binding Capacity of Haemoglobin in Patients with Severe Respiratory Disease journal December 1981
Accurate bond and angle parameters for X-ray protein structure refinement journal July 1991
Coot model-building tools for molecular graphics journal November 2004
MolProbity : all-atom structure validation for macromolecular crystallography journal December 2009
PHENIX: a comprehensive Python-based system for macromolecular structure solution journal January 2010
Crystal structure of 3-hydroxyanthranilic acid 3,4-dioxygenase from Saccharomyces cerevisiae: A special subgroup of the type III extradiol dioxygenases journal March 2006
Prokaryotic Homologs of the Eukaryotic 3-Hydroxyanthranilate 3,4-Dioxygenase and 2-Amino-3-Carboxymuconate-6-Semialdehyde Decarboxylase in the 2-Nitrobenzoate Degradation Pathway of Pseudomonas fluorescens Strain KU-7 journal March 2003
Tryptophan Catabolism: Identification and Characterization of a New Degradative Pathway journal November 2005
PHENIX: a comprehensive Python-based system for macromolecular structure solution. text January 2010

Cited By (1)

Quaternary structure of α-amino-β-carboxymuconate-ϵ-semialdehyde decarboxylase (ACMSD) controls its activity journal June 2019

Similar Records

Observing 3-hydroxyanthranilate-3,4-dioxygenase in action through a crystalline lens
Journal Article · Thu Jul 30 00:00:00 EDT 2020 · Proceedings of the National Academy of Sciences of the United States of America · OSTI ID:1651144

An Iron Reservoir to the Catalytic Metal: THE RUBREDOXIN IRON IN AN EXTRADIOL DIOXYGENASE
Journal Article · Mon Apr 27 00:00:00 EDT 2015 · Journal of Biological Chemistry · OSTI ID:1418602

Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center
Journal Article · Thu Dec 31 23:00:00 EST 2020 · Journal of Biological Chemistry · OSTI ID:1778798