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