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Literature summary for 2.5.1.34 extracted from

  • Mai, P.; Zocher, G.; Ludwig, L.; Stehle, T.; Li, S.
    Actions of tryptophan prenyltransferases toward fumiquinazolines and their potential application for the generation of prenylated derivatives by combining chemical and chemoenzymatic syntheses (2016), Adv. Synth. Catal., 358, 1639 -1653.
No PubMed abstract available
Search for more literature for 2.5.1.34

Application

Application Comment Organism
synthesis possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 4-DMATS, overview Aspergillus fumigatus

Protein Variants

Protein Variants Comment Organism
M328L site-directed mutagenesis, the FgaPT2 mutant shows increased activity with L-tyrosine compared to the wild-type enzyme Aspergillus fumigatus
Y398F site-directed mutagenesis, the FgaPT2 mutant shows increased activity with L-tyrosine compared to the wild-type enzyme Aspergillus fumigatus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.011
-
 ent-ardeemin fumiquinazoline pH 7.5, 37°C, wild-type enzyme Aspergillus fumigatus
0.032
-
 ardeemin fumiquinazoline pH 7.5, 37°C, wild-type enzyme Aspergillus fumigatus
0.055
-
 dia-ardeemin fumiquinazoline pH 7.5, 37°C, wild-type enzyme 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
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dimethylallyl diphosphate + ardeemin fumiquinazoline
-
 Aspergillus fumigatus diphosphate + (1S,4R)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
 ?
dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline
-
 Aspergillus fumigatus diphosphate + (1R,4R)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
 ?
dimethylallyl diphosphate + dia-ardeemin fumiquinazoline
-
 Aspergillus fumigatus diphosphate + (1S,4S)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
 ?
dimethylallyl diphosphate + ent-ardeemin fumiquinazoline
-
 Aspergillus fumigatus diphosphate + (1R,4S)-4-methyl-1-[[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
 ?
dimethylallyl diphosphate + L-tryptophan
-
 Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
 ?
dimethylallyl diphosphate + L-tyrosine low activity with the wild-type enzyme, higher activity with the enzyme mutantsM328L and Y398F Aspergillus fumigatus diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
-
 ?

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

Temperature Stability [°C]

Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
37
-
 purified enzyme, pH 7.5, 4 h, 20% activity remaining Aspergillus fumigatus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.0016
-
 ent-ardeemin fumiquinazoline pH 7.5, 37°C, wild-type enzyme Aspergillus fumigatus
0.009
-
 ardeemin fumiquinazoline pH 7.5, 37°C, wild-type enzyme Aspergillus fumigatus
0.009
-
 dia-ardeemin fumiquinazoline pH 7.5, 37°C, wild-type enzyme Aspergillus fumigatus

pH Optimum

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

General Information

General Information Comment Organism
metabolism dimethylallyltryptophan synthases (DMATSs) catalyze regiospecific transfer reactions of a prenyl moiety from dimethylallyl diphosphate to various positions of the indole ring of tryptophan. The 4-DMATS enzyme FgaPT2 is involved in biosynthesis of fumigaclavine C Aspergillus fumigatus
additional information possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 4-DMATS, docking study of FgaPT2 with ardeemin fumiquinazoline and its stereoisomers, overview Aspergillus fumigatus