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Literature summary for 2.5.1.34 extracted from

  • Luk, L.Y.; Qian, Q.; Tanner, M.E.
    A cope rearrangement in the reaction catalyzed by dimethylallyltryptophan synthase? (2011), J. Am. Chem. Soc., 133, 12342-12345.
    View publication on PubMed
Search for more literature for 2.5.1.34

Protein Variants

Protein Variants Comment Organism
E89A site-directed mutagenesis, the mutant shows a 17% reduction in kcat compared to the wild-type enzyme Aspergillus fumigatus
E89Q site-directed mutagenesis, the mutant shows a 400fold reduction in kcat compared to the wild-type enzyme Aspergillus fumigatus
K174A site-directed mutagenesis, the mutant shows a 31fold reduction in kcat compared to the wild-type enzyme Aspergillus fumigatus
K174Q site-directed mutagenesis, the mutant shows a 20fold reduction in kcat compared to the wild-type enzyme Aspergillus fumigatus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0067
-
 L-tryptophan wild-type enzyme, pH and temperature not specified in the publication Aspergillus fumigatus
0.0068
-
 L-tryptophan mutant E89Q, pH and temperature not specified in the publication Aspergillus fumigatus
0.0086
-
 L-tryptophan mutants K174Q and K175A, pH and temperature not specified in the publication Aspergillus fumigatus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
dimethylallyl diphosphate + L-tryptophan Aspergillus fumigatus
-
 diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
 r

Organism

Organism UniProt Comment Textmining
Aspergillus fumigatus
-
-
-

Reaction

Reaction Comment Organism Reaction ID
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan Cope mechanism for the reaction catalyzed by DMAT synthase, overview Aspergillus fumigatus
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dimethylallyl diphosphate + L-tryptophan
-
 Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
 r
dimethylallyl diphosphate + L-tryptophan cleavage of the C-O bond in DMAPP is reversible Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
 r
additional information the dimethylallyltryptophan synthase catalyzes the normal prenylation of Trp at C-4. The Lys174Ala mutant produces a hexahydropyrroloindole alkaloid that is reverse-prenylated at C-3 as its major product, by a mechanism that involves an initial reverse-prenylation at C-3, followed by a Cope rearrangement and rearomatization Aspergillus fumigatus ?
-
 ?

Synonyms

Synonyms Comment Organism
FgaPT2
-
 Aspergillus fumigatus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.001
-
 L-tryptophan below, mutant E89A, pH and temperature not specified in the publication Aspergillus fumigatus
0.001
-
 dimethylallyl diphosphate below, mutant E89A, pH and temperature not specified in the publication Aspergillus fumigatus
0.015
-
 L-tryptophan mutant E89Q, pH and temperature not specified in the publication Aspergillus fumigatus
0.015
-
 dimethylallyl diphosphate mutant E89Q, pH and temperature not specified in the publication Aspergillus fumigatus
0.023
-
 L-tryptophan mutant K174A, pH and temperature not specified in the publication Aspergillus fumigatus
0.023
-
 dimethylallyl diphosphate mutant K174A, pH and temperature not specified in the publication Aspergillus fumigatus
0.39
-
 L-tryptophan mutant K174Q, pH and temperature not specified in the publication Aspergillus fumigatus
0.39
-
 dimethylallyl diphosphate mutant K174Q, pH and temperature not specified in the publication Aspergillus fumigatus
0.47
-
 L-tryptophan wild-type enzyme, pH and temperature not specified in the publication Aspergillus fumigatus
0.47
-
 dimethylallyl diphosphate wild-type enzyme, pH and temperature not specified in the publication Aspergillus fumigatus

General Information

General Information Comment Organism
metabolism the enzyme catalyzes the first step of ergot alkaloid biosynthesis Aspergillus fumigatus