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PMID: 17428786 Published · ppublish English Journal Article

The structure of 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase provides insights into the mechanism of uric acid degradation.

The Journal of biological chemistry ·Vol. 282 ·No. 25 ·2007-06-22 ·Pages 18182-18189

Cendron L, Berni R, Folli C, Ramazzina I, Percudani R, Zanotti G

Abstract

The complete degradation of uric acid to (S)-allantoin, as recently elucidated, involves three enzymatic reactions. Inactivation by pseudogenization of the genes of the pathway occurred during hominoid evolution, resulting in a high concentration of urate in the blood and susceptibility to gout. Here, we describe the 1.8A resolution crystal structure of the homodimeric 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase, which catalyzes the last step in the urate degradation pathway, for both ligand-free enzyme and enzyme in complex with the substrate analogs (R)-allantoin and guanine. Each monomer comprises ten alpha-helices, grouped into two domains and assembled in a novel fold. The structure and the mutational analysis of the active site have allowed us to identify some residues that are essential for catalysis, among which His-67 and Glu-87 appear to play a particularly significant role. Glu-87 may facilitate the exit of the carboxylate group because of electrostatic repulsion that destabilizes the ground state of the substrate, whereas His-67 is likely to be involved in a protonation step leading to the stereoselective formation of the (S)-allantoin enantiomer as reaction product. The structural and functional characterization of 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase can provide useful information in view of the potential use of this enzyme in the enzymatic therapy of gout.

MeSH Terms
Allantoin/pharmacology Amino Acid Sequence Animals Carboxy-Lyases/chemistry,physiology Crystallography, X-Ray DNA Mutational Analysis Glutamic Acid/chemistry Guanine/pharmacology Histidine/chemistry Ligands Models, Chemical Molecular Sequence Data Protein Folding Uric Acid/metabolism Zebrafish Zebrafish Proteins/chemistry,physiology
Chemicals
Ligands Zebrafish Proteins Uric Acid Allantoin Glutamic Acid Histidine Guanine 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase, zebrafish Carboxy-Lyases
Authors & Affiliations
6 authors, click to expand affiliations / ORCID
Cendron Laura
Department of Chemistry, University of Padua, and Instituto di Chimica Biomolecolare-Consiglio Nazionale delle Ricerche, Section of Padua, Via Marzolo 1, 35131 Padua, Italy; Venetian Institute of Molecular Medicine, Via Orus 2, 35127 Padua, Italy.
Berni Rodolfo
Department of Biochemistry and Molecular Biology, University of Parma, Viale delle Scienze 23/A, 43100 Parma, Italy.
Folli Claudia
Department of Biochemistry and Molecular Biology, University of Parma, Viale delle Scienze 23/A, 43100 Parma, Italy.
Ramazzina Ileana
Department of Biochemistry and Molecular Biology, University of Parma, Viale delle Scienze 23/A, 43100 Parma, Italy.
Percudani Riccardo
Department of Biochemistry and Molecular Biology, University of Parma, Viale delle Scienze 23/A, 43100 Parma, Italy. Electronic address: [email protected].
Zanotti Giuseppe
Department of Chemistry, University of Padua, and Instituto di Chimica Biomolecolare-Consiglio Nazionale delle Ricerche, Section of Padua, Via Marzolo 1, 35131 Padua, Italy; Venetian Institute of Molecular Medicine, Via Orus 2, 35127 Padua, Italy. Electronic address: [email protected].
Article Info
Journal
The Journal of biological chemistry
Abbr.
J Biol Chem
ISSN
0021-9258
Published
2007-06-22
Epub
2007-00-11
Pages
18182-18189
Language
English
Region
United States
NLM ID
2985121R
Subset
IM
Databases
GENBANK
EF197726
PDB
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