Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 1.13.11.46 extracted from

  • Shah, D.; Conrad, J.; Moran, G.
    Intermediate partitioning kinetic isotope effects for the NIH shift of 4-hydroxyphenylpyruvate dioxygenase and the hydroxylation reaction of hydroxymandelate synthase reveal mechanistic complexity (2013), Biochemistry, 52, 6097-6107.
    View publication on PubMed
Search for more literature for 1.13.11.46

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression of wild-type and mutant enzymes Amycolatopsis orientalis

Protein Variants

Protein Variants Comment Organism
S201A site-directed mutagenesis, the mutant enzyme produces 3% 4-hydroxyphenylacetate, and 97% 4-hydroxymandelate, the benzylic carbon retains predominant sp3 character in the TS for the initial hydrogen abstraction Amycolatopsis orientalis

Metals/Ions

Metals/Ions Comment Organism Structure
Fe2+ a Fe(II)-dependent dioxygenase Amycolatopsis orientalis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4-hydroxyphenylpyruvate + O2 Amycolatopsis orientalis
-
 4-hydroxymandelate + CO2
-
 ?

Organism

Organism UniProt Comment Textmining
Amycolatopsis orientalis
-
 gene AOHMS
-

Purification (Commentary)

Purification (Comment) Organism
recombinant wild-type and mutant enzymes by ammonium sulfate fractionation, anion echange chromatography, and gel filtration Amycolatopsis orientalis

Reaction

Reaction Comment Organism Reaction ID
4-hydroxyphenylpyruvate + O2 = (S)-4-hydroxymandelate + CO2 reaction mechanism, overview Amycolatopsis orientalis
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-hydroxyphenylpyruvate + O2
-
 Amycolatopsis orientalis 4-hydroxymandelate + CO2
-
 ?

Synonyms

Synonyms Comment Organism
HMS
-
 Amycolatopsis orientalis
hydroxymandelate synthase
-
 Amycolatopsis orientalis

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Amycolatopsis orientalis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
 assay at Amycolatopsis orientalis

General Information

General Information Comment Organism
evolution 4-hydroxyphenylpyruvate dioxygenase, HPPD, EC 1.13.11.27, and hydroxymandelate synthase catalyze similar reactions using the same substrates, 4-hydroxyphenylpyruvate and dioxygen. Initially, both enzymes reduce and activate dioxygen in order to decarboxylate 4-hydroxyphenylpyruvate, yielding 4-hydroxyphenylacetate, CO2, and an activated oxo intermediate. Both enzymes then hydroxylate 4-hydroxyphenylacetate but do so in different positions Amycolatopsis orientalis