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Literature summary 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)

EC Number Cloned (Comment) Organism
2.5.1.34 gene 4-DMATS, sequence comparison Aspergillus fumigatus
2.5.1.80 DNA and amino acid sequence determination and analysis, sequence comparisons, recombinant expression of His6-tagged enzyme in Escherichia coli strain XL-1 Blue MRF' from vector pQE30-dmatsNeo Neosartorya sp.

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.5.1.34 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]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.5.1.34 0.052
-
dimethylallyl diphosphate pH 7.5, 37°C Aspergillus fumigatus
2.5.1.34 0.081
-
L-abrine pH 7.5, 37°C Aspergillus fumigatus
2.5.1.34 0.238
-
L-tryptophan pH 7.5, 37°C Aspergillus fumigatus
2.5.1.34 0.416
-
5-methyl-DL-tryptophan pH 7.5, 37°C Aspergillus fumigatus
2.5.1.34 2.876
-
L-tryptophan methyl ester pH 7.5, 37°C Aspergillus fumigatus
2.5.1.80 additional information
-
additional information Michaelis-Menten kinetics Neosartorya sp.
2.5.1.80 0.052
-
dimethylallyl diphosphate pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.081
-
L-abrine pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.238
-
L-tryptophan pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.416
-
5-methyl-DL-tryptophan pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 2.876
-
L-tryptophan methyl ester pH 7.5, 37°C, recombinant enzyme Neosartorya sp.

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.5.1.34 Ca2+ activates, required Aspergillus fumigatus
2.5.1.34 Mg2+ activates, required Aspergillus fumigatus
2.5.1.34 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
2.5.1.80 Ca2+ required Neosartorya sp.
2.5.1.80 Mg2+ required Neosartorya sp.

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.5.1.80 50000
-
-
Neosartorya sp.
2.5.1.80 53000
-
-
Neosartorya sp.

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.34 dimethylallyl diphosphate + L-tryptophan Aspergillus fumigatus
-
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + L-tryptophan Neosartorya sp.
-
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.34 Aspergillus fumigatus Q50EL0 gene 4-DMATS
-
2.5.1.80 Neosartorya sp.
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.5.1.80 recombinant His6-tagged enzyme from Escherichia coli strain XL-1 Blue MRF' by nickel affinity chromatography to homogeneity Neosartorya sp.

Reaction

EC Number Reaction Comment Organism Reaction ID
2.5.1.34 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
2.5.1.80 dimethylallyl diphosphate + L-tryptophan = diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan catalytic reaction mechanism involving Glu138, overview Neosartorya sp.

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.34 4-dimethylallyl-indole-3-lactic acid 10.5% of the activity with L-Trp Aspergillus fumigatus ?
-
?
2.5.1.34 4-dimethylallyl-indole-3-pyruvic acid 29.4% of the activity with L-Trp Aspergillus fumigatus ?
-
?
2.5.1.34 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
-
?
2.5.1.34 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
-
?
2.5.1.34 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
-
?
2.5.1.34 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
-
?
2.5.1.34 dimethylallyl diphosphate + D-tryptophan 9.7% of the activity with L-Trp Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + indole-3-propionic acid 32.2% of the activity with L-Trp Aspergillus fumigatus ?
-
?
2.5.1.34 dimethylallyl diphosphate + L-abrine
-
Aspergillus fumigatus ?
-
?
2.5.1.34 dimethylallyl diphosphate + L-abrine 58.0% of the activity with L-Trp Aspergillus fumigatus ?
-
?
2.5.1.34 dimethylallyl diphosphate + L-tryptophan
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + L-tryptophan methyl ester
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
?
2.5.1.34 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
-
?
2.5.1.34 dimethylallyl diphosphate + tryptamine 4.6% of the activity with L-Trp Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-tryptamine
-
?
2.5.1.34 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 ?
-
?
2.5.1.80 dimethylallyl diphosphate + 4-methyl-DL-tryptophan
-
Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-4-methyl-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
-
Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-5-methoxy-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 5-methyl-DL-tryptophan
-
Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 6-methyl-DL-tryptophan
-
Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + L-abrine
-
Neosartorya sp. diphosphate + ?
-
?
2.5.1.80 dimethylallyl diphosphate + L-tryptophan
-
Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + L-tryptophan methyl ester
-
Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
?
2.5.1.80 dimethylallyl diphosphate + N-acetyl-DL-tryptophan
-
Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-N-acetyl-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + tryptamine
-
Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-tryptamine
-
?
2.5.1.80 additional information 7-DMATSNeo accepts not only L-tryptophan but also simple indole derivatives as substrates. The retention of the amino group of L-tryptophan appears to be an essential factor for molecular recognition by 7-DMATSNeo. No or poor activity with D-tryptophan, 5-hydroxy-L-tryptophan, indole-3-propionic acid, indole-3-pyruvic acid, DL-indole-3-lactic acid, glycyl-L-tryptophan, and cyclo(glycyl-L-tryptophan). No activity with 5-hydoroxy-L-tryptophan, 7-methyl-DL-tryptophan, 6-fluoro-DL-tryptophan, and 1-methyl-DL-tryptophan. Mass spectrometric product identification and analysis, overview Neosartorya sp. ?
-
?

Subunits

EC Number Subunits Comment Organism
2.5.1.80 ? x * 50000, about, recombinant His6-tagged enzyme, SDS-PAGE, x * 53000, about, sequence calculation Neosartorya sp.

Synonyms

EC Number Synonyms Comment Organism
2.5.1.34 4-DMATS
-
Aspergillus fumigatus
2.5.1.34 FgaPT2
-
Aspergillus fumigatus
2.5.1.80 7-dimethylallyl tryptophan synthase
-
Neosartorya sp.
2.5.1.80 7-DMATS
-
Neosartorya sp.
2.5.1.80 7-DMATSNeo
-
Neosartorya sp.

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.5.1.34 37
-
assay at Aspergillus fumigatus
2.5.1.80 37
-
assay at Neosartorya sp.

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.5.1.34 0.043
-
L-abrine pH 7.5, 37°C Aspergillus fumigatus
2.5.1.34 0.108
-
L-tryptophan pH 7.5, 37°C Aspergillus fumigatus
2.5.1.34 0.117
-
L-tryptophan methyl ester pH 7.5, 37°C Aspergillus fumigatus
2.5.1.34 0.125
-
5-methyl-DL-tryptophan pH 7.5, 37°C Aspergillus fumigatus
2.5.1.34 0.917
-
dimethylallyl diphosphate pH 7.5, 37°C Aspergillus fumigatus
2.5.1.80 0.043
-
L-abrine pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.092
-
dimethylallyl diphosphate pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.108
-
L-tryptophan pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.112
-
L-tryptophan methyl ester pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.125
-
5-methyl-DL-tryptophan pH 7.5, 37°C, recombinant enzyme Neosartorya sp.

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.5.1.34 7.5
-
assay at Aspergillus fumigatus
2.5.1.80 7.5
-
assay at Neosartorya sp.

General Information

EC Number General Information Comment Organism
2.5.1.34 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
2.5.1.34 additional information comparison of the three-dimensional structural models of 7-DMATSNeo from Neosartorya sp. with FgaPT2 (4-DMATS) from Aspergillus fumigatus Aspergillus fumigatus
2.5.1.34 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
2.5.1.80 additional information analysis of the structural basis of the regioselective prenylation of L-tryptophan at the C7 position by comparison of the three-dimensional structural models of 7-DMATSNeo with FgaPT2 (4-DMATS), EC 2.5.1.34, from Aspergillus fumigatus. Construction of three-dimensional structural models of 7 DMATSNeo and FgaPT2 (4-DMATS). Docking studies of potential substrates, overview. Residues F129, L130, E138, F226, F243 are involved in binding of L-tryptophan, residue Y393 is involved in stabilization of the allylic cation via cation-Pi interactions. Residues R154, K239, Y241, R311, K313, K391, Y393, K454, and Y460 are involved in diphosphate coordination Neosartorya sp.

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.5.1.80 0.038
-
L-tryptophan methyl ester pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.3
-
5-methyl-DL-tryptophan pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.47
-
L-tryptophan pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 0.542
-
L-abrine pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
2.5.1.80 1.76
-
dimethylallyl diphosphate pH 7.5, 37°C, recombinant enzyme Neosartorya sp.