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Nuclear magnetic resonance and molecular modeling study on mycophenolic acid: implications for binding to inosine monophosphate dehydrogenase.
The conformation of the sodium salt of mycophenolic acid (MPA), a potent inhibitor of inosine monophosphate dehydrogenase (IMPD), derived from 1D DIFNOE and 2D ROESY experiments in water and molecular dynamics (MD) is described. The hexenoic acid side chain conformation consistent with the NMR data was similar to that seen in the X-ray structure of MPA. The solution conformation was applied in a molecular modeling study in order to explore the potential features of enzyme binding. Our results, based on striking similarities in molecular volume and electrostatic isopotential between MPA and cofactor NAD+, lead to the suggestion that MPA is capable of binding to the nicotinamide site of IMPD and mimicking the NAD+ inverse regulation of the enzyme. In addition, our proposed model is in good agreement with the observed high affinity of the dinucleotide analogues thiazole- and selenazole-4-carboxamide adenine dinucleotide to IMPD.
Authors : Makara G M , Keserû G M , Kajtár-Peredy M , Anderson W K ,
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Pathways :
WP1615: 3-Chloroacrylic acid degradation
WP1621: Arginine and proline metabolism
WP1647: Fatty acid biosynthesis
WP1654: gamma-Hexachlorocyclohexane degradation
WP1666: Linoleic acid metabolism
WP1008: amino acid conjugation of benzoic acid
WP1020: Fatty Acid Biosynthesis
WP105: Fatty Acid Beta Oxidation 2
WP1061: Fatty Acid Beta Oxidation
WP1068: Nuclear Receptors
WP1075: Folic Acid Network
WP1099: Nuclear receptors in lipid metabolism and toxicity
WP1107: Mitochondrial LC-Fatty Acid Beta-Oxidation
WP1127: amino acid conjugation of benzoic acid
WP1139: Fatty Acid Biosynthesis
WP1177: Fatty Acid Beta Oxidation
WP1184: Nuclear Receptors
WP1192: Folic Acid Network
WP1207: Fatty Acid Beta Oxidation
WP121: Colanic Acid Building Blocks Biosynthesis
WP1226: Mitochondrial LC-Fatty Acid Beta-Oxidation
WP1228: Fatty Acid Biosynthesis
WP1237: Fatty Acid Beta Oxidation
WP1252: amino acid conjugation of benzoic acid
WP126: Fatty Acid Beta Oxidation 1
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