Application | Comment | Organism |
---|---|---|
synthesis | potential usage of tryptophan prenylating enzymes as biocatalysts for Friedel-Crafts alkylation | Aspergillus clavatus |
synthesis | potential usage of tryptophan prenylating enzymes as biocatalysts for Friedel-Crafts alkylation | Streptomyces coelicolor |
Cloned (Comment) | Organism |
---|---|
gene SCO7467, recombinant expression of His8-tagged enzyme in Escherichia coli strain BL21(DE3) | Streptomyces coelicolor |
KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
additional information | - |
additional information | Michaelis-Menten kinetics | Aspergillus clavatus | |
additional information | - |
additional information | Michaelis-Menten kinetics | Streptomyces coelicolor | |
0.028 | - |
2-pentenyl diphosphate | pH 7.5, 37°C | Streptomyces coelicolor | |
0.04 | - |
benzyl diphosphate | pH 7.5, 37°C | Aspergillus clavatus | |
0.05 | - |
dimethylallyl diphosphate | pH 7.5, 37°C | Streptomyces coelicolor | |
0.054 | - |
methylallyl diphosphate | pH 7.5, 37°C | Streptomyces coelicolor | |
0.076 | - |
dimethylallyl diphosphate | pH 7.5, 37°C | Aspergillus clavatus | |
0.11 | - |
benzyl diphosphate | pH 7.5, 37°C | Streptomyces coelicolor | |
0.12 | - |
methylallyl diphosphate | pH 7.5, 37°C | Aspergillus clavatus | |
0.13 | - |
2-pentenyl diphosphate | pH 7.5, 37°C | Aspergillus clavatus |
Metals/Ions | Comment | Organism | Structure |
---|---|---|---|
Ca2+ | required | Aspergillus clavatus | |
Ca2+ | required | Streptomyces coelicolor |
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 | - |
? | |
dimethylallyl diphosphate + L-tryptophan | Streptomyces coelicolor | - |
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + L-tryptophan | Streptomyces coelicolor A3(2) | - |
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Aspergillus clavatus | - |
- |
- |
Streptomyces coelicolor | Q9ADJ2 | gene SCO7467 | - |
Streptomyces coelicolor A3(2) | Q9ADJ2 | gene SCO7467 | - |
Purification (Comment) | Organism |
---|---|
recombinant His8-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography | Streptomyces coelicolor |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
2-pentenyl diphosphate + L-tryptophan | C-5, C-6 and C-7 prenylation | Streptomyces coelicolor | diphosphate + 5-(pent-2-enyl)-L-tryptophan | - |
? | |
2-pentenyl diphosphate + L-tryptophan | C-5, C-6 and C-7 prenylation | Streptomyces coelicolor A3(2) | diphosphate + 5-(pent-2-enyl)-L-tryptophan | - |
? | |
2-pentenyl diphosphate + L-tryptophan | C-5, C-6 and C-7 prenylation | Streptomyces coelicolor | diphosphate + 6-(pent-2-enyl)-L-tryptophan | - |
? | |
2-pentenyl diphosphate + L-tryptophan | C-6 prenylation | Aspergillus clavatus | diphosphate + 6-(pent-2-enyl)-L-tryptophan | - |
? | |
2-pentenyl diphosphate + L-tryptophan | C-5, C-6 and C-7 prenylation | Streptomyces coelicolor A3(2) | diphosphate + 6-(pent-2-enyl)-L-tryptophan | - |
? | |
2-pentenyl diphosphate + L-tryptophan | C-5, C-6 and C-7 prenylation | Streptomyces coelicolor | diphosphate + 7-(pent-2-enyl)-L-tryptophan | - |
? | |
benzyl diphosphate + L-tryptophan | C-5 prenylation | Aspergillus clavatus | diphosphate + 5-benzyl-L-tryptophan | - |
? | |
benzyl diphosphate + L-tryptophan | C-6 prenylation | Aspergillus clavatus | diphosphate + 6-benzyl-L-tryptophan | - |
? | |
benzyl diphosphate + L-tryptophan | C-6 prenylation | Streptomyces coelicolor | diphosphate + 6-benzyl-L-tryptophan | - |
? | |
dimethylallyl diphosphate + 1-methyl-L-tryptophan | 46.9% of the activity with L-Trp | Aspergillus clavatus | diphosphate + 1-methyl-5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + 4-methyl-L-tryptophan | 56.6% of the activity with L-Trp | Aspergillus clavatus | diphosphate + 4-methyl-5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + 6-fluoro-L-tryptophan | 69.5% of the activity with L-Trp | Aspergillus clavatus | diphosphate + 6-fluoro-5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + 6-methyl-L-tryptophan | 53.2% of the activity with L-Trp | Aspergillus clavatus | diphosphate + 6-methyl-5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + 6-[(2E)-pent-2-en-1-yl]-L-tryptophan | - |
Streptomyces coelicolor | diphosphate + 7-[(2E)-pent-2-en-1-yl]-L-tryptophan + 5-[(2E)-pent-2-en-1-yl]-L-tryptophan | - |
? | |
dimethylallyl diphosphate + 7-methyl-DL-tryptophan | 57.8% of the activity with L-Trp | Aspergillus clavatus | diphosphate + 7-methyl-5-(3-methylbut-2-enyl)-DL-tryptophan | - |
? | |
dimethylallyl diphosphate + beta-homo-L-tryptophan | 48.8% of the activity with L-Trp | Aspergillus clavatus | ? | - |
? | |
dimethylallyl diphosphate + DL-indole-3-lactic acid | 67.3% of the activity with L-Trp | Aspergillus clavatus | ? | - |
? | |
dimethylallyl diphosphate + indole-3-propionic acid | 70.7% of the activity with L-Trp | Aspergillus clavatus | ? | - |
? | |
dimethylallyl diphosphate + L-abrine | 90.9% of the activity with L-Trp | Aspergillus clavatus | ? | - |
? | |
dimethylallyl diphosphate + L-o-Tyr | C-3 prenylation | Aspergillus clavatus | diphosphate + 5-(3-methylbut-2-enyl)-L-o-tyrosine | 3-dimethylallyl-L-tyrosine | ? | |
dimethylallyl diphosphate + L-tryptophan | - |
Aspergillus clavatus | diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + L-tryptophan | - |
Streptomyces coelicolor | diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + L-tryptophan | best substrate | Aspergillus clavatus | diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + L-tryptophan | best substrate | Streptomyces coelicolor | diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + L-tryptophan | - |
Streptomyces coelicolor A3(2) | diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + L-tryptophan | best substrate | Streptomyces coelicolor A3(2) | diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
dimethylallyl diphosphate + N-acetyl-DL-tryptophan | 54.4% of the activity with L-Trp | Aspergillus clavatus | diphosphate + N-acetyl-5-(3-methylbut-2-enyl)-DL-tryptophan | - |
? | |
dimethylallyl diphosphate + trans-indole-3-acrylic acid | 38.0% of the activity with L-Trp | Aspergillus clavatus | ? | - |
? | |
methylallyl diphosphate + L-tryptophan | C-5 and C-6 prenylation | Aspergillus clavatus | diphosphate + 5-(but-2-enyl)-L-tryptophan | - |
? | |
methylallyl diphosphate + L-tryptophan | C-5, C-6 and C-7 prenylation | Streptomyces coelicolor | diphosphate + 5-(but-2-enyl)-L-tryptophan | - |
? | |
methylallyl diphosphate + L-tryptophan | C-5 and C-6 prenylation | Aspergillus clavatus | diphosphate + 6-(but-2-enyl)-L-tryptophan | - |
? | |
methylallyl diphosphate + L-tryptophan | C-5, C-6 and C-7 prenylation | Streptomyces coelicolor | diphosphate + 6-(but-2-enyl)-L-tryptophan | - |
? | |
methylallyl diphosphate + L-tryptophan | C-5, C-6 and C-7 prenylation | Streptomyces coelicolor | diphosphate + 7-(but-2-enyl)-L-tryptophan | - |
? | |
additional information | no or poor activity with 5-methyl-DL-Trp, 5-bromo-DL-Trp, L-m-Tyr, and 6-[(2E)-pent-2-en-1-yl]-L-tryptophan. The enzyme catalyzes regiospecific prenylations of indolocarbazoles at the para-position of the indole N-atom. Molecular dynamics simulation experiments with a homologous model of 5-DMATS explain well its reactions with methylallyl and 2-pentenyl diphosphate. Comparison of bacterial and fungal alkylation/benzylation reactions by investigations on 5-DMATS from Aspergillus clavatus and 5-DMATSSc from Streptomyces coelicolor. Homology modelling of 5-DMATS, overview | Aspergillus clavatus | ? | - |
? | |
additional information | substrate specificity, overview. Molecular dynamics simulation experiments with a homologous model of 5-DMATS explain well its reactions with methylallyl and 2-pentenyl diphosphate. Comparison of bacterial and fungal alkylation/benzylation reactions by investigations on 5-DMATS from Aspergillus clavatus and 5-DMATSSc from Streptomyces coelicolor. Homology modelling of 5-DMATS, overview | Streptomyces coelicolor | ? | - |
? | |
additional information | substrate specificity, overview. Molecular dynamics simulation experiments with a homologous model of 5-DMATS explain well its reactions with methylallyl and 2-pentenyl diphosphate. Comparison of bacterial and fungal alkylation/benzylation reactions by investigations on 5-DMATS from Aspergillus clavatus and 5-DMATSSc from Streptomyces coelicolor. Homology modelling of 5-DMATS, overview | Streptomyces coelicolor A3(2) | ? | - |
? |
Synonyms | Comment | Organism |
---|---|---|
5-DMATS | - |
Aspergillus clavatus |
5-DMATSSc | - |
Streptomyces coelicolor |
SCO7467 | - |
Streptomyces coelicolor |
tryptophan C5-prenyltransferase | - |
Aspergillus clavatus |
tryptophan C5-prenyltransferase | - |
Streptomyces coelicolor |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
37 | - |
assay at | Aspergillus clavatus |
37 | - |
assay at | Streptomyces coelicolor |
Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
0.00028 | - |
benzyl diphosphate | pH 7.5, 37°C | Streptomyces coelicolor | |
0.00048 | - |
methylallyl diphosphate | pH 7.5, 37°C | Streptomyces coelicolor | |
0.0014 | - |
2-pentenyl diphosphate | pH 7.5, 37°C | Streptomyces coelicolor | |
0.0015 | - |
methylallyl diphosphate | pH 7.5, 37°C | Aspergillus clavatus | |
0.005 | - |
benzyl diphosphate | pH 7.5, 37°C | Aspergillus clavatus | |
0.023 | - |
2-pentenyl diphosphate | pH 7.5, 37°C | Aspergillus clavatus | |
0.4 | - |
dimethylallyl diphosphate | pH 7.5, 37°C | Streptomyces coelicolor | |
1.3 | - |
dimethylallyl diphosphate | pH 7.5, 37°C | Aspergillus clavatus |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
7.5 | - |
assay at | Aspergillus clavatus |
7.5 | - |
assay at | Streptomyces coelicolor |
General Information | Comment | Organism |
---|---|---|
additional information | molecular dynamics simulation experiments with a homologous model of 5-DMATS, overview | Aspergillus clavatus |
additional information | molecular dynamics simulation experiments with a homologous model of 5-DMATS, overview | Streptomyces coelicolor |