|
KEGG pathways | MAP code | Pathways |
---|
MAP00350 | Tyrosine metabolism | MAP00360 | Phenylalanine metabolism |
UniProtKB:Accession Number | P80064 | Q53586 | O48604 | P93836 |
---|
Entry name | HPPD_PSEUJ | HPPD_STRAW | HPPD_HORVU | HPPD_ARATH |
---|
Activity | 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2). | 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2). | 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2). | 4-hydroxyphenylpyruvate + O(2) = homogentisate + CO(2). |
---|
Subunit | Homotetramer. | Homodimer. |
| Homodimer. |
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Subcellular location |
|
| Cytoplasm (By similarity). | Cytoplasm. |
---|
Cofactor | Binds 1 iron ion per subunit. | Binds 1 iron ion per subunit. | Binds 1 iron ion per subunit (By similarity). | Binds 1 iron ion per subunit. |
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Compound table: links to PDB-related databases & PoSSuM |
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| Cofactors | Substrates | Products | intermediates |
---|
KEGG-id | C00023 | C00007 | C01179 | C00011 | C00544 |
|
---|
Compound | Iron | O2 | 3-(4-Hydroxyphenyl)pyruvate | CO2 | Homogentisate |
|
---|
Type | heavy metal | others | aromatic ring (only carbon atom),carbohydrate,carboxyl group | others | aromatic ring (only carbon atom),carboxyl group |
|
---|
ChEBI | 18248 82664
| 15379 26689 27140
| 15999
| 16526
| 44747
|
|
---|
PubChem | 23925
| 977
| 979
| 280
| 780
|
|
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| | | | | | | | | | | | | |
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1cjxA01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1cjxB01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1cjxC01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1cjxD01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1t47A01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1t47B01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp8A01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp8B01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp8C01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp8D01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp9A01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp9B01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sqdA01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1tfzA01 |  |  |  |  |  |  |  | Unbound | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1cjxA02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-ACT |
---|
1cjxB02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-ACT |
---|
1cjxC02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-ACT |
---|
1cjxD02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-ACT |
---|
1t47A02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-NTD |
---|
1t47B02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:FE2-NTD |
---|
1sp8A02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp8B02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp8C02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp8D02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp9A02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sp9B02 |  |  |  |  |  |  |  | Bound:FE2 | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1sqdA02 |  |  |  |  |  |  |  | Bound:_FE | Unbound | Unbound | Unbound | Unbound | Unbound |
---|
1tfzA02 |  |  |  |  |  |  |  | Bound:_FE | Unbound | Unbound | Unbound | Unbound | Intermediate-analogue:_FE-869 |
---|
References for Catalytic Mechanism | References | Sections | No. of steps in catalysis |
---|
[2] | Fig.4, Scheme I, p.3162-3164 |
| [6] | Scheme 1, Scheme 2, p.1459-1460 |
| [7] | p.979-981 |
| [13] | Scheme 2, Scheme 3, Scheme 4, p.12334-12336 |
| [15] | Scheme 2C, Scheme 3 |
|
references | [1] |
---|
PubMed ID | 7274212 |
---|
Journal | Eur J Biochem |
---|
Year | 1981 |
---|
Volume | 117 |
---|
Pages | 311-8 |
---|
Authors | Leinberger R, Hull WE, Simon H, Retey J |
---|
Title | Steric course of the NIH shift in the enzymic formation of homogentisic acid. |
---|
[2] |
---|
PubMed ID | 4027238 |
---|
Journal | Biochemistry |
---|
Year | 1985 |
---|
Volume | 24 |
---|
Pages | 3158-65 |
---|
Authors | Pascal RA Jr, Oliver MA, Chen YC |
---|
Title | Alternate substrates and inhibitors of bacterial 4-hydroxyphenylpyruvate dioxygenase. |
---|
[3] |
---|
PubMed ID | 3017941 |
---|
Journal | J Biol Chem |
---|
Year | 1986 |
---|
Volume | 261 |
---|
Pages | 11693-6 |
---|
Authors | Bradley FC, Lindstedt S, Lipscomb JD, Que L Jr, Roe AL, Rundgren M |
---|
Title | 4-Hydroxyphenylpyruvate dioxygenase is an iron-tyrosinate protein. |
---|
[4] |
---|
PubMed ID | 1572351 |
---|
Journal | Eur J Biochem |
---|
Year | 1992 |
---|
Volume | 205 |
---|
Pages | 459-66 |
---|
Authors | Ruetschi U, Odelhog B, Lindstedt S, Barros-Soderling J, Persson B, Jornvall H |
---|
Title | Characterization of 4-hydroxyphenylpyruvate dioxygenase. Primary structure of the Pseudomonas enzyme. |
---|
[5] |
---|
PubMed ID | 7597701 |
---|
Journal | Toxicol Appl Pharmacol |
---|
Year | 1995 |
---|
Volume | 133 |
---|
Pages | 12-9 |
---|
Authors | Ellis MK, Whitfield AC, Gowans LA, Auton TR, Provan WM, Lock EA, Smith LL |
---|
Title | Inhibition of 4-hydroxyphenylpyruvate dioxygenase by 2-(2-nitro-4-trifluoromethylbenzoyl)-cyclohexane-1,3-dione and 2-(2-chloro-4-methanesulfonylbenzoyl)-cyclohexane-1,3-dione. |
---|
[6] |
---|
PubMed ID | 10465420 |
---|
Journal | Bioorg Med Chem |
---|
Year | 1999 |
---|
Volume | 7 |
---|
Pages | 1459-65 |
---|
Authors | Ling TS, Shiu S, Yang DY |
---|
Title | Design and synthesis of 3-fluoro-2-oxo-3-phenylpropionic acid derivatives as potent inhibitors of 4-hydroxyphenylpyruvate dioxygenase from pig liver. |
---|
[7] |
---|
Comments | X-ray crystallography |
---|
PubMed ID | 10467142 |
---|
Journal | Structure Fold Des |
---|
Year | 1999 |
---|
Volume | 7 |
---|
Pages | 977-88 |
---|
Authors | Serre L, Sailland A, Sy D, Boudec P, Rolland A, Pebay-Peyroula E, Cohen-Addad C |
---|
Title | Crystal structure of Pseudomonas fluorescens 4-hydroxyphenylpyruvate dioxygenase: an enzyme involved in the tyrosine degradation pathway. |
---|
Related PDB | 1cjx |
---|
[8] |
---|
PubMed ID | 10853644 |
---|
Journal | Bioorg Med Chem Lett |
---|
Year | 2000 |
---|
Volume | 10 |
---|
Pages | 843-5 |
---|
Authors | Lin YL, Wu CS, Lin SW, Yang DY |
---|
Title | SAR studies of 2-o-substituted-benzoyl- and 2-alkanoyl-cyclohexane-1,3-diones as inhibitors of 4-hydroxyphenylpyruvate dioxygenase. |
---|
[9] |
---|
PubMed ID | 12067543 |
---|
Journal | Bioorg Med Chem Lett |
---|
Year | 2002 |
---|
Volume | 12 |
---|
Pages | 1709-13 |
---|
Authors | Lin YL, Huang JL, Wu CS, Liu HG, Yang DY |
---|
Title | Design, synthesis, and evaluation of postulated transient intermediate and substrate analogues as inhibitors of 4-hydroxyphenylpyruvate dioxygenase. |
---|
[10] |
---|
PubMed ID | 12014960 |
---|
Journal | J Med Chem |
---|
Year | 2002 |
---|
Volume | 45 |
---|
Pages | 2222-8 |
---|
Authors | Wu CS, Huang JL, Sun YS, Yang DY |
---|
Title | Mode of action of 4-hydroxyphenylpyruvate dioxygenase inhibition by triketone-type inhibitors. |
---|
[11] |
---|
PubMed ID | 12031447 |
---|
Journal | Phytochemistry |
---|
Year | 2002 |
---|
Volume | 60 |
---|
Pages | 281-8 |
---|
Authors | Meazza G, Scheffler BE, Tellez MR, Rimando AM, Romagni JG, Duke SO, Nanayakkara D, Khan IA, Abourashed EA, Dayan FE |
---|
Title | The inhibitory activity of natural products on plant p-hydroxyphenylpyruvate dioxygenase. |
---|
[12] |
---|
PubMed ID | 12939152 |
---|
Journal | Biochemistry |
---|
Year | 2003 |
---|
Volume | 42 |
---|
Pages | 10238-45 |
---|
Authors | Kavana M, Moran GR |
---|
Title | Interaction of (4-hydroxyphenyl)pyruvate dioxygenase with the specific inhibitor 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione. |
---|
[13] |
---|
PubMed ID | 15379572 |
---|
Journal | Biochemistry |
---|
Year | 2004 |
---|
Volume | 43 |
---|
Pages | 12331-42 |
---|
Authors | Borowski T, Bassan A, Siegbahn PE |
---|
Title | 4-Hydroxyphenylpyruvate dioxygenase: a hybrid density functional study of the catalytic reaction mechanism. |
---|
[14] |
---|
PubMed ID | 15157070 |
---|
Journal | Biochemistry |
---|
Year | 2004 |
---|
Volume | 43 |
---|
Pages | 6370-7 |
---|
Authors | Brownlee JM, Johnson-Winters K, Harrison DH, Moran GR |
---|
Title | Structure of the ferrous form of (4-hydroxyphenyl)pyruvate dioxygenase from Streptomyces avermitilis in complex with the therapeutic herbicide, NTBC. |
---|
Related PDB | 1t47 |
---|
[15] |
---|
PubMed ID | 14730970 |
---|
Journal | Biochemistry |
---|
Year | 2004 |
---|
Volume | 43 |
---|
Pages | 663-74 |
---|
Authors | Gunsior M, Ravel J, Challis GL, Townsend CA |
---|
Title | Engineering p-hydroxyphenylpyruvate dioxygenase to a p-hydroxymandelate synthase and evidence for the proposed benzene oxide intermediate in homogentisate formation. |
---|
[16] |
---|
PubMed ID | 15301540 |
---|
Journal | Biochemistry |
---|
Year | 2004 |
---|
Volume | 43 |
---|
Pages | 10414-23 |
---|
Authors | Yang C, Pflugrath JW, Camper DL, Foster ML, Pernich DJ, Walsh TA |
---|
Title | Structural basis for herbicidal inhibitor selectivity revealed by comparison of crystal structures of plant and mammalian 4-hydroxyphenylpyruvate dioxygenases. |
---|
Related PDB | 1sqd,1tfz |
---|
[17] |
---|
PubMed ID | 15070344 |
---|
Journal | J Am Chem Soc |
---|
Year | 2004 |
---|
Volume | 126 |
---|
Pages | 4486-7 |
---|
Authors | Neidig ML, Kavana M, Moran GR, Solomon EI |
---|
Title | CD and MCD studies of the non-heme ferrous active site in (4-hydroxyphenyl)pyruvate dioxygenase: correlation between oxygen activation in the extradiol and alpha-KG-dependent dioxygenases. |
---|
[18] |
---|
PubMed ID | 15084729 |
---|
Journal | Plant Physiol |
---|
Year | 2004 |
---|
Volume | 134 |
---|
Pages | 1388-400 |
---|
Authors | Fritze IM, Linden L, Freigang J, Auerbach G, Huber R, Steinbacher S |
---|
Title | The crystal structures of Zea mays and Arabidopsis 4-hydroxyphenylpyruvate dioxygenase. |
---|
Related PDB | 1sp8,1sp9 |
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created | updated |
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2004-10-28 | 2009-09-29 |
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