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

BRENDA support

Literature summary for 2.5.1.34 extracted from

  • Miyamoto, K.; Ishikawa, F.; Nakamura, S.; Hayashi, Y.; Nakanishi, I.; Kakeya, H.
    A 7-dimethylallyl tryptophan synthase from a fungal Neosartorya sp.: biochemical characterization and structural insight into the regioselective prenylation (2014), Bioorg. Med. Chem., 22, 2517-2528.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene 4-DMATS, sequence comparison Aspergillus fumigatus

Crystallization (Commentary)

Crystallization (Comment) Organism
the crystal structure of FgaPT2 (4-DMATS) is determined as a complex with its aromatic substrate L-tryptophan and with dimethylallyl S-thiolodiphosphate (DMSPP), an analogue of its isoprenoid substrate dimethylallyl diphosphate, X-ray structural analysis and three-dimensional structural modeling Aspergillus fumigatus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.052
-
dimethylallyl diphosphate pH 7.5, 37°C Aspergillus fumigatus
0.081
-
L-abrine pH 7.5, 37°C Aspergillus fumigatus
0.238
-
L-tryptophan pH 7.5, 37°C Aspergillus fumigatus
0.416
-
5-methyl-DL-tryptophan pH 7.5, 37°C Aspergillus fumigatus
2.876
-
L-tryptophan methyl ester pH 7.5, 37°C Aspergillus fumigatus

Metals/Ions

Metals/Ions Comment Organism Structure
Ca2+ activates, required Aspergillus fumigatus
Mg2+ activates, required Aspergillus fumigatus
additional information Trp-DMATS is capable of catalyzing prenylation without the requirement of Mg2+, a unique characteristic that distinguishes the Trp-DMATS family of prenyl transferases 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
-
?

Organism

Organism UniProt Comment Textmining
Aspergillus fumigatus Q50EL0 gene 4-DMATS
-

Reaction

Reaction Comment Organism Reaction ID
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan the mechanism of this enzyme-catalyzed Friedel–Crafts reaction represents strict regioselectivity at the C4 position of the indole ring of L-tryptophan, proposed reaction mechanism for Aspergillus fummigatus FgaPT2 involving Glu89 and Lys174 Aspergillus fumigatus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-dimethylallyl-indole-3-lactic acid 10.5% of the activity with L-Trp Aspergillus fumigatus ?
-
?
4-dimethylallyl-indole-3-pyruvic acid 29.4% of the activity with L-Trp Aspergillus fumigatus ?
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan 21.0% of the activity with L-Trp Aspergillus fumigatus diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan 8.1% of the activity with L-Trp Aspergillus fumigatus diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan 15.2% of the activity with L-Trp Aspergillus fumigatus diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan 16.3% of the activity with L-Trp Aspergillus fumigatus diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
dimethylallyl diphosphate + D-tryptophan 9.7% of the activity with L-Trp Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
-
?
dimethylallyl diphosphate + indole-3-propionic acid 32.2% of the activity with L-Trp Aspergillus fumigatus ?
-
?
dimethylallyl diphosphate + L-abrine
-
Aspergillus fumigatus ?
-
?
dimethylallyl diphosphate + L-abrine 58.0% of the activity with L-Trp Aspergillus fumigatus ?
-
?
dimethylallyl diphosphate + L-tryptophan
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester 7.2% of the activity with L-Trp Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
?
dimethylallyl diphosphate + tryptamine 4.6% of the activity with L-Trp Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-tryptamine
-
?
additional information no or poor activity with 1-methyl-L-tryptophan, 4-methyl-DL-tryptophan, 6-fluoro-DL-tryptophan, 5-methoxy-L-tryptophan, idole-3-acetic acid, N-acetyl-DL-tryptophan, and cyclo-L-Trp-Gly, substrate specificity, docking study and molecular modelling, overview Aspergillus fumigatus ?
-
?

Synonyms

Synonyms Comment Organism
4-DMATS
-
Aspergillus fumigatus
FgaPT2
-
Aspergillus fumigatus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Aspergillus fumigatus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.043
-
L-abrine pH 7.5, 37°C Aspergillus fumigatus
0.108
-
L-tryptophan pH 7.5, 37°C Aspergillus fumigatus
0.117
-
L-tryptophan methyl ester pH 7.5, 37°C Aspergillus fumigatus
0.125
-
5-methyl-DL-tryptophan pH 7.5, 37°C Aspergillus fumigatus
0.917
-
dimethylallyl diphosphate pH 7.5, 37°C Aspergillus fumigatus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Aspergillus fumigatus

General Information

General Information Comment Organism
evolution Trp-DMATS is capable of catalyzing prenylation without the requirement of Mg2+, a unique characteristic that distinguishes the Trp-DMATS family of prenyl transferases Aspergillus fumigatus
additional information comparison of the three-dimensional structural models of 7-DMATSNeo from Neosartorya sp. with FgaPT2 (4-DMATS) from Aspergillus fumigatus Aspergillus fumigatus
physiological function FgaPT2 plays a role in the first pathway-specific enzyme during ergot alkaloids biosynthesis and catalyzes the regular prenylation of L-tryptophan at the C4 position Aspergillus fumigatus