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Literature summary for 2.5.1.B31 extracted from
- Actions of tryptophan prenyltransferases toward fumiquinazolines and their potential application for the generation of prenylated derivatives by combining chemical and chemoenzymatic syntheses (2016), Adv. Synth. Catal., 358, 1639 -1653.
No PubMed abstract available
Application
| Application | Comment | Organism |
|---|---|---|
| synthesis | possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 5-DMATS, overview | Aspergillus clavatus |
| synthesis | possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 5-DMATSSc, overview | Streptomyces coelicolor |
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| recombinant overexpression | Streptomyces coelicolor |
| recombinant overexpression | Aspergillus clavatus |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.2 | - |
ent-ardeemin fumiquinazoline | pH 7.5, 37°C, wild-type enzyme | Streptomyces coelicolor |  |
| 0.2 | - |
ent-ardeemin fumiquinazoline | pH 7.5, 37°C, wild-type enzyme | Aspergillus clavatus | |
| 0.21 | - |
ardeemin fumiquinazoline | pH 7.5, 37°C, wild-type enzyme | Streptomyces coelicolor | |
| 0.21 | - |
ardeemin fumiquinazoline | pH 7.5, 37°C, wild-type enzyme | Aspergillus clavatus | |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| Ca2+ | required | Streptomyces coelicolor | |
| Ca2+ | required | 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 | - |
? | |
| dimethylallyl diphosphate + L-tryptophan | Streptomyces coelicolor | - |
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | the product is further processed to 5-dimethylallylindole-3-acetonitrile | ? | |
| additional information | Aspergillus clavatus | dimethylallyltryptophan synthases (DMATSs) catalyze regiospecific transfer reactions of a prenyl moiety from dimethylallyl diphosphate to various positions of the indole ring of tryptophan | ? | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Aspergillus clavatus | - |
gene 5-DMATS | - |
| Streptomyces coelicolor | - |
gene 5-DMATS | - |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant enzyme | Streptomyces coelicolor |
| recombinant enzyme | Aspergillus clavatus |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| dimethylallyl diphosphate + ardeemin fumiquinazoline | - |
Aspergillus clavatus | diphosphate + (1S,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione | - |
? | |
| dimethylallyl diphosphate + ardeemin fumiquinazoline | - |
Streptomyces coelicolor | diphosphate + (1S,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-1-[[5,6-bis(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-4-methyl-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione | - |
? | |
| dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline | - |
Aspergillus clavatus | diphosphate + (1R,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione | - |
? | |
| dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline | - |
Streptomyces coelicolor | diphosphate + (1R,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione | - |
? | |
| dimethylallyl diphosphate + dia-ardeemin fumiquinazoline | - |
Aspergillus clavatus | diphosphate + (1S,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione | - |
? | |
| dimethylallyl diphosphate + dia-ardeemin fumiquinazoline | - |
Streptomyces coelicolor | diphosphate + (1S,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione | - |
? | |
| dimethylallyl diphosphate + ent-ardeemin fumiquinazoline | - |
Aspergillus clavatus | diphosphate + (1R,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione | - |
? | |
| dimethylallyl diphosphate + ent-ardeemin fumiquinazoline | - |
Streptomyces coelicolor | diphosphate + (1R,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-1-[[5,6-bis(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-4-methyl-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione | - |
? | |
| dimethylallyl diphosphate + L-tryptophan | - |
Streptomyces coelicolor | diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan | - |
? | |
| 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 | the product is further processed to 5-dimethylallylindole-3-acetonitrile | ? | |
| dimethylallyl diphosphate + L-tyrosine | - |
Streptomyces coelicolor | diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine | - |
? | |
| dimethylallyl diphosphate + L-tyrosine | - |
Aspergillus clavatus | diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine | - |
? | |
| additional information | dimethylallyltryptophan synthases (DMATSs) catalyze regiospecific transfer reactions of a prenyl moiety from dimethylallyl diphosphate to various positions of the indole ring of tryptophan | Aspergillus clavatus | ? | - |
? | |
| additional information | 5-DMATS catalyzes regiospecific prenylation of analogues of ardeemin fumiquinazoline. Synthesis of ardeemin fumiquinazoline, a precursor of the multidrug resistance export pump inhibitor ardeemin, and its stereoisomers, LC-MS analysis of reaction products, overview | Aspergillus clavatus | ? | - |
? | |
| additional information | 5-DMATSSc catalyzes regiospecific prenylation of analogues of ardeemin fumiquinazoline. Synthesis of ardeemin FQ, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, and its stereoisomers, LC-MS analysis of reaction products, overview | Streptomyces coelicolor | ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| 5-DMATS | - |
Aspergillus clavatus |
| 5-DMATSSc | - |
Streptomyces coelicolor |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 37 | - |
assay at | Streptomyces coelicolor |
| 37 | - |
assay at | Aspergillus clavatus |
Temperature Stability [°C]
| Temperature Stability Minimum [°C] | Temperature Stability Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 37 | - |
purified recombinant enzyme, loss of 50% activity after 20 min, loss of over 90% activity after 60 min, inactivation after 120 min | Streptomyces coelicolor |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.022 | - |
ent-ardeemin fumiquinazoline | pH 7.5, 37°C, wild-type enzyme | Streptomyces coelicolor | |
| 0.022 | - |
ent-ardeemin fumiquinazoline | pH 7.5, 37°C, wild-type enzyme | Aspergillus clavatus | |
| 0.027 | - |
ardeemin fumiquinazoline | pH 7.5, 37°C, wild-type enzyme | Streptomyces coelicolor | |
| 0.027 | - |
ardeemin fumiquinazoline | pH 7.5, 37°C, wild-type enzyme | Aspergillus clavatus | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.5 | - |
assay at | Streptomyces coelicolor |
| 7.5 | - |
assay at | Aspergillus clavatus |
General Information
| General Information | Comment | Organism |
|---|---|---|
| metabolism | enzyme 5-DMATSSc enzyme is involved in biosynthesis of dimethylallylindole 3-acetonitrile | Streptomyces coelicolor |
| additional information | possibility of producing prenylated analogues of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, by using dimethylallydiphosphate transferase enzymes, e.g. 5-DMATSSc | Streptomyces coelicolor |
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