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Literature summary extracted from

  • Schindler, C.E.M.; Hollenbach, E.; Mietzner, T.; Schleifer, K.J.; Zacharias, M.
    Free energy calculations elucidate substrate binding, gating mechanism, and tolerance-promoting mutations in herbicide target 4-hydroxyphenylpyruvate dioxygenase (2019), Protein Sci., 28, 1048-1058 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.13.11.27 a ligand-mediated conformational switch in helix H11 mediates rapid substrate access followed by active site closing and efficient product release through H11 opening. In mutant HPPD, large differences in H11 gating are found with correlation to experimentally measured herbicide tolerance Zea mays
1.13.11.27 a ligand-mediated conformational switch in helix H11 mediates rapid substrate access followed by active site closing and efficient product release through H11 opening. In mutant HPPD, large differences in H11 gating are found with correlation to experimentally measured herbicide tolerance Arabidopsis thaliana

Protein Variants

EC Number Protein Variants Comment Organism
1.13.11.27 M335H/P336A/E363Q residues 336 and 363 are substituted by the corresponding residues of Zea mays HPPD, more than twofold increase in IC50 for sulcotrione and tembotrione. Increased herbicide tolerance compared to wild-type matches with a clear shift in the free energy profile toward favoring the closed helix H11 state Zea mays
1.13.11.27 M335H/P336A/E363Q residues 336 and 363 are substituted by the corresponding residues of Zea mays HPPD, more than twofold increase in IC50 for sulcotrione and tembotrione. Increased herbicide tolerance compared to wild-type matches with a clear shift in the free energy profile toward favoring the closed helix H11 state Arabidopsis thaliana
1.13.11.27 M335H/P336A/P339T/T341D/E363Q/E426Q substitutions correspond to residues found in Zea mays. The mutant has a clear preference for the closed H11 state Zea mays
1.13.11.27 M335H/P336A/P339T/T341D/E363Q/E426Q substitutions correspond to residues found in Zea mays. The mutant has a clear preference for the closed H11 state Arabidopsis thaliana

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.27 bicyclopyrone
-
 Arabidopsis thaliana
1.13.11.27 bicyclopyrone
-
 Zea mays
1.13.11.27 isoxaflutole
-
 Arabidopsis thaliana
1.13.11.27 isoxaflutole
-
 Zea mays
1.13.11.27 mesotrione
-
 Arabidopsis thaliana
1.13.11.27 mesotrione
-
 Zea mays
1.13.11.27 sulcotrione
-
 Arabidopsis thaliana
1.13.11.27 sulcotrione
-
 Zea mays
1.13.11.27 tembotrione
-
 Arabidopsis thaliana
1.13.11.27 tembotrione
-
 Zea mays
1.13.11.27 topramezone
-
 Arabidopsis thaliana
1.13.11.27 topramezone
-
 Zea mays

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.13.11.27 0.077
-
 4-hydroxyphenylpyruvate wild-type, pH 7,20°C Arabidopsis thaliana
1.13.11.27 0.098
-
 4-hydroxyphenylpyruvate mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7,20°C Arabidopsis thaliana
1.13.11.27 0.134
-
 4-hydroxyphenylpyruvate mutant M335H/P336A/E363Q, pH 7,20°C Arabidopsis thaliana
1.13.11.27 0.32
-
 4-hydroxyphenylpyruvate pH 7,20°C Zea mays

Organism

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

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.27 4-hydroxyphenylpyruvate + O2
-
 Zea mays homogentisate + CO2
-
 ?
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 0.116
-
 4-hydroxyphenylpyruvate mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7,20°C Arabidopsis thaliana
1.13.11.27 0.177
-
 4-hydroxyphenylpyruvate mutant M335H/P336A/E363Q, pH 7,20°C Arabidopsis thaliana
1.13.11.27 0.183
-
 4-hydroxyphenylpyruvate wild-type, pH 7,20°C Arabidopsis thaliana
1.13.11.27 0.51
-
 4-hydroxyphenylpyruvate pH 7,20°C Zea mays

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.11.27 0.0000013
-
 wild-type, pH 7, 20°C Arabidopsis thaliana topramezone
1.13.11.27 0.0000013
-
 wild-type, pH 7, 20°C Arabidopsis thaliana isoxaflutole
1.13.11.27 0.0000016
-
 mutant M335H/P336A/E363Q, pH 7, 20°C Arabidopsis thaliana topramezone
1.13.11.27 0.0000017
-
 wild-type, pH 7, 20°C Arabidopsis thaliana sulcotrione
1.13.11.27 0.0000018
-
 wild-type, pH 7, 20°C Arabidopsis thaliana mesotrione
1.13.11.27 0.0000022
-
 wild-type, pH 7, 20°C Arabidopsis thaliana tembotrione
1.13.11.27 0.0000025
-
 mutant M335H/P336A/E363Q, pH 7, 20°C Arabidopsis thaliana isoxaflutole
1.13.11.27 0.0000027
-
 mutant M335H/P336A/E363Q, pH 7, 20°C Arabidopsis thaliana mesotrione
1.13.11.27 0.000004
-
 mutant M335H/P336A/E363Q, pH 7, 20°C Arabidopsis thaliana tembotrione
1.13.11.27 0.0000041
-
 mutant M335H/P336A/E363Q, pH 7, 20°C Arabidopsis thaliana sulcotrione
1.13.11.27 0.0000051
-
 wild-type, pH 7, 20°C Arabidopsis thaliana bicyclopyrone
1.13.11.27 0.0000061
-
 mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C Arabidopsis thaliana topramezone
1.13.11.27 0.0000068
-
 mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C Arabidopsis thaliana mesotrione
1.13.11.27 0.0000072
-
 pH 7, 20°C Zea mays topramezone
1.13.11.27 0.0000075
-
 mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C Arabidopsis thaliana isoxaflutole
1.13.11.27 0.0000087
-
 pH 7, 20°C Zea mays tembotrione
1.13.11.27 0.00001
-
 mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C Arabidopsis thaliana tembotrione
1.13.11.27 0.000012
-
 mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C Arabidopsis thaliana sulcotrione
1.13.11.27 0.000015
-
 mutant M335H/P336A/E363Q, pH 7, 20°C Arabidopsis thaliana bicyclopyrone
1.13.11.27 0.000023
-
 pH 7, 20°C Zea mays bicyclopyrone
1.13.11.27 0.000042
-
 pH 7, 20°C Zea mays isoxaflutole
1.13.11.27 0.000043
-
 mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C Arabidopsis thaliana bicyclopyrone
1.13.11.27 0.000062
-
 pH 7, 20°C Zea mays mesotrione
1.13.11.27 0.000094
-
 pH 7, 20°C Zea mays sulcotrione