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Literature summary for 2.5.1.B31 extracted from

  • Yu, X.; Liu, Y.; Xie, X.; Zheng, X.D.; Li, S.M.
    Biochemical characterization of indole prenyltransferases: filling the last gap of prenylation positions by a 5-dimethylallyltryptophan synthase from Aspergillus clavatus (2012), J. Biol. Chem., 287, 1371-1380.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
gene ACLA_031240 or 5-dmats, DNA and amino acid sequence determination and analysis, expression as solube His-tagged protein in Escherichia coli strain M15, subcloning in Escherichia coli strain XL1 Blue Aspergillus clavatus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.034
-
L-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.076
-
dimethylallyl diphosphate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.1
-
1-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.25
-
4-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.26
-
L-abrine pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.27
-
6-fluoro-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.35
-
N-acetyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.39
-
indole-3-propionate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.4
-
trans-indole-3-acrylate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.47
-
7-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.67
-
DL-indole-3-lactate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.97
-
L-beta-homotryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
1
-
6-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus

Metals/Ions

Metals/Ions Comment Organism Structure
Ca2+ required, activates 2.5fold Aspergillus clavatus
Mg2+ activates 2fold Aspergillus clavatus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
dimethylallyl diphosphate + L-tryptophan Aspergillus clavatus
-
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
?

Organism

Organism UniProt Comment Textmining
Aspergillus clavatus A1CRX0 gene ACLA_031240 or 5-dmats
-

Purification (Commentary)

Purification (Comment) Organism
recombinant solube His-tagged 5-DMATS from Escherichia coli strain M15 by nickel affinity chromatography to near homogeneity Aspergillus clavatus

Reaction

Reaction Comment Organism Reaction ID
dimethylallyl diphosphate + L-tryptophan = diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan 5-dimethylallyltryptophan synthase performs the highly regiospecific regular prenylation at C-5 of the indole nucleus of the simple indole derivatives Aspergillus clavatus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dimethylallyl diphosphate + 1-methyl-DL-tryptophan
-
Aspergillus clavatus diphosphate + 1-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
-
Aspergillus clavatus diphosphate + 4-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
-
?
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
-
Aspergillus clavatus diphosphate + 6-fluoro-5-(3-methylbut-2-en-1-yl)tryptophan
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
-
Aspergillus clavatus diphosphate + 6-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
-
Aspergillus clavatus diphosphate + 7-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
-
?
dimethylallyl diphosphate + DL-indole-3-lactate
-
Aspergillus clavatus diphosphate + 2-hydroxy-3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid
-
?
dimethylallyl diphosphate + indole-3-propionate
-
Aspergillus clavatus diphosphate + 3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid
-
?
dimethylallyl diphosphate + L-abrine
-
Aspergillus clavatus diphosphate + N-methyl-5-(3-methylbut-2-en-1-yl)-L-tryptophan
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
-
Aspergillus clavatus diphosphate + (3S)-3-amino-4-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]butanoic acid
-
?
dimethylallyl diphosphate + L-tryptophan
-
Aspergillus clavatus diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan
-
Aspergillus clavatus diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan product analysis by mass spectrometry and NMR ?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
-
Aspergillus clavatus diphosphate + N-acetyl-5-(3-methylbut-2-en-1-yl)tryptophan
-
?
dimethylallyl diphosphate + trans-indole-3-acrylate
-
Aspergillus clavatus diphosphate + (2E)-3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]prop-2-enoic acid
-
?
additional information in presence of dimethylallyl diphosphate, the recombinant enzyme accepts simple indole derivatives with L-tryptophan as the best substrate, it is also active with tryptophan-containing cyclic dipeptides but with much lower conversion yields. No activity with geranyl or farnesyl diphosphate Aspergillus clavatus ?
-
?

Synonyms

Synonyms Comment Organism
5-DMATS
-
Aspergillus clavatus
EAW08391
-
Aspergillus clavatus

Temperature Optimum [°C]

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

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.059
-
1-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.1
-
N-acetyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.14
-
trans-indole-3-acrylate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.15
-
L-beta-homotryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.29
-
6-fluoro-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.29
-
4-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.39
-
indole-3-propionate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.4
-
7-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.4
-
L-abrine pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.43
-
DL-indole-3-lactate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.76
-
6-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.87
-
L-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
1.3
-
dimethylallyl diphosphate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus

pH Optimum

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

General Information

General Information Comment Organism
evolution 5-DMATS belongs to the DMATS superfamily, indole prenyltransferases with different prenylation positions, overview Aspergillus clavatus

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.155
-
L-beta-homotryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.286
-
N-acetyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.35
-
trans-indole-3-acrylate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.59
-
1-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.642
-
DL-indole-3-lactate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.76
-
6-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
0.851
-
7-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
1
-
indole-3-propionate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
1.074
-
6-fluoro-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
1.16
-
4-methyl-DL-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
1.538
-
dimethylallyl diphosphate pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
1.538
-
L-abrine pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus
25.59
-
L-tryptophan pH 7.5, 37°C, recombinant His-tagged 5-DMATS Aspergillus clavatus