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Literature summary extracted from

  • Lin, H.; Chen, X.; Chen, J.; Wang, D.; Wu, F.; Lin, S.; Zhan, C.; Wu, J.; Yang, W.; Yang, G.
    Crystal structure of 4-hydroxyphenylpyruvate dioxygenase in complex with substrate reveals a new starting point for herbicide discovery (2019), Research (Wash. D.C.), 2019, 2602414 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.13.11.27 structure of HPPD in complex with substrate 4-hydroxyphenylpyruvate at a resolution of 2.80 A. 4-Hydroxyphenylpyruvate takes keto rather than enol form inside the HPPD active pocket. Residues Phe424, Asn423, Glu394, Gln307, Asn282, and Ser267 play important roles in substrate binding and catalytic cycle. Residue Gln293 undergoes a rotation upon the HPPA binding and forms H-bond network of Ser267-Asn282-Gln307-Gln293, resulting in the transformation of HPPD from an inactive state to active state Arabidopsis thaliana

Protein Variants

EC Number Protein Variants Comment Organism
1.13.11.27 F381A residue is involved in substrate binding Arabidopsis thaliana
1.13.11.27 N282A residue is involved in substrate binding Arabidopsis thaliana
1.13.11.27 N423A residue is involved in substrate binding Arabidopsis thaliana
1.13.11.27 Q293A residue is involved in substrate binding Arabidopsis thaliana
1.13.11.27 Q307A residue is involved in substrate binding Arabidopsis thaliana
1.13.11.27 S267A residue is involved in substrate binding Arabidopsis thaliana

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.27 3-(2,6-dimethylphenyl)-1-methyl-6-(2-oxidanyl-6-oxidanylidene-cyclohexen-1-yl)carbonyl-quinazoline-2,4-dione competitive inhibitor with respect to HPPA with the characteristic of slow binding and lower potency against human enzyme Arabidopsis thaliana

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.13.11.27 0.00187
-
 4-hydroxyphenylpyruvate wild-type, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.0053
-
 4-hydroxyphenylpyruvate mutant S267A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.0091
-
 4-hydroxyphenylpyruvate mutant F381A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.0108
-
 4-hydroxyphenylpyruvate mutant N282A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.0157
-
 4-hydroxyphenylpyruvate mutant N423A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.0303
-
 4-hydroxyphenylpyruvate mutant Q307A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.0904
-
 4-hydroxyphenylpyruvate mutant Q293A, pH 7, 25°C Arabidopsis thaliana

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.27 Arabidopsis thaliana P93836
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.27 4-hydroxyphenylpyruvate + O2
-
 Arabidopsis thaliana homogentisate + CO2
-
 ?

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.13.11.27 0.014
-
 4-hydroxyphenylpyruvate mutant Q293A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.039
-
 4-hydroxyphenylpyruvate mutant N282A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.176
-
 4-hydroxyphenylpyruvate mutant Q307A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.249
-
 4-hydroxyphenylpyruvate mutant S267A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.545
-
 4-hydroxyphenylpyruvate mutant N423A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 0.924
-
 4-hydroxyphenylpyruvate mutant F381A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 1.079
-
 4-hydroxyphenylpyruvate wild-type, pH 7, 25°C Arabidopsis thaliana

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.13.11.27 0.0000242
-
 3-(2,6-dimethylphenyl)-1-methyl-6-(2-oxidanyl-6-oxidanylidene-cyclohexen-1-yl)carbonyl-quinazoline-2,4-dione pH 7, 25°C Arabidopsis thaliana

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.13.11.27 0.15
-
 4-hydroxyphenylpyruvate mutant Q293A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 3.6
-
 4-hydroxyphenylpyruvate mutant N282A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 5.8
-
 4-hydroxyphenylpyruvate mutant Q307A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 34.8
-
 4-hydroxyphenylpyruvate mutant N423A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 46.7
-
 4-hydroxyphenylpyruvate mutant S267A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 101.5
-
 4-hydroxyphenylpyruvate mutant F381A, pH 7, 25°C Arabidopsis thaliana
1.13.11.27 577
-
 4-hydroxyphenylpyruvate wild-type, pH 7, 25°C Arabidopsis thaliana