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Literature summary for 2.5.1.80 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
Search for more literature for 2.5.1.80

Cloned(Commentary)

Cloned (Comment) Organism
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.

KM Value [mM]

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

Metals/Ions

Metals/Ions Comment Organism Structure
Ca2+ required Neosartorya sp.
Mg2+ required Neosartorya sp.

Molecular Weight [Da]

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

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
dimethylallyl diphosphate + L-tryptophan Neosartorya sp.
-
 diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
 ?

Organism

Organism UniProt Comment Textmining
Neosartorya sp.
-
-
-

Purification (Commentary)

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

Reaction

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
-
 Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-4-methyl-DL-tryptophan
-
 ?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
-
 Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-5-methoxy-DL-tryptophan
-
 ?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
-
 Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
-
 ?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
-
 Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
-
 ?
dimethylallyl diphosphate + L-abrine
-
 Neosartorya sp. diphosphate + ?
-
 ?
dimethylallyl diphosphate + L-tryptophan
-
 Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
 ?
dimethylallyl diphosphate + L-tryptophan methyl ester
-
 Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
 ?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
-
 Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-N-acetyl-DL-tryptophan
-
 ?
dimethylallyl diphosphate + tryptamine
-
 Neosartorya sp. diphosphate + 7-(3-methylbut-2-enyl)-tryptamine
-
 ?
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

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

Synonyms

Synonyms Comment Organism
7-dimethylallyl tryptophan synthase
-
 Neosartorya sp.
7-DMATS
-
 Neosartorya sp.
7-DMATSNeo
-
 Neosartorya sp.

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Neosartorya sp.

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, recombinant enzyme Neosartorya sp.
0.092
-
 dimethylallyl diphosphate pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
0.108
-
 L-tryptophan pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
0.112
-
 L-tryptophan methyl ester pH 7.5, 37°C, recombinant enzyme Neosartorya sp.
0.125
-
 5-methyl-DL-tryptophan pH 7.5, 37°C, recombinant enzyme Neosartorya sp.

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Neosartorya sp.

General Information

General Information Comment Organism
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]

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