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Literature summary extracted from

  • Liebhold, M.; Xie, X.; Li, S.M.
    Expansion of enzymatic Friedel-Crafts alkylation on indoles: acceptance of unnatural beta-unsaturated allyl diphospates by dimethylallyl-tryptophan synthases (2012), Org. Lett., 14, 4882-4885.
    View publication on PubMed

Application

EC Number Application Comment Organism
2.5.1.B31 additional information prenyltransferases of the dimethylallyl-tryptophan synthase superfamily catalyze Friedel-Crafts alkylation with high flexibility for aromatic substrates, but the high specificity for dimethylallyl diphosphate prohibits their application as biocatalysts Aspergillus clavatus
2.5.1.34 additional information prenyltransferases of the dimethylallyl-tryptophan synthase superfamily catalyze Friedel-Crafts alkylation with high flexibility for aromatic substrates, but the high specificity for dimethylallyl diphosphate prohibits their application as biocatalysts Aspergillus fumigatus

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.5.1.B31 0.04
-
methylallyl diphosphate 37°C, pH not specified in the publication Aspergillus clavatus
2.5.1.B31 0.131
-
2-pentenyl diphosphate 37°C, pH not specified in the publication Aspergillus clavatus
2.5.1.34 0.04
-
methylallyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus
2.5.1.34 0.056
-
2-pentenyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.B31 dimethylallyl diphosphate + L-tryptophan Aspergillus clavatus
-
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + L-tryptophan Aspergillus fumigatus
-
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.B31 Aspergillus clavatus
-
-
-
2.5.1.34 Aspergillus fumigatus
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
2.5.1.34 dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan reaction mechanism and substrate specificity, overview Aspergillus fumigatus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.B31 2-pentenyl diphosphate + L-tryptophan 91% of the activity with dimethylallyl diphosphate Aspergillus clavatus diphosphate + 6-(2-trans-pentenyl)-L-tryptophan
-
?
2.5.1.B31 dimethylallyl diphosphate + L-tryptophan
-
Aspergillus clavatus diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.B31 methylallyl diphosphate + L-tryptophan 22% of the activity with dimethylallyl diphosphate Aspergillus clavatus diphosphate + 5-(2-trans-butenyl)-L-tryptophan + 6-(2-trans-butenyl)-L-tryptophan
-
?
2.5.1.B31 additional information no activity with 3-methylbutanyl diphosphate and 4-methyl-3-pentenyl diphosphate. Product identification with NMR spectroscopy Aspergillus clavatus ?
-
?
2.5.1.34 2-pentenyl diphosphate + L-tryptophan very low activity, the alkylation shifts from C-4 to C-5 for FgaPT2, which can be explained by the longer chain length and thus deeper extension of 2-pentenyl diphosphate into the reaction chamber in comparison to that of dimethylallyl diphosphate, so that C-1' of the alkyl residue is closer to C-5 than C-4 in FgaPT2 Aspergillus fumigatus diphosphate + 5-(2-trans-pentenyl)-L-tryptophan
-
?
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 dimethylallyl diphosphate is the preferred substrate Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.34 methylallyl diphosphate + L-tryptophan very low activity Aspergillus fumigatus diphosphate + 4-(2-trans-butenyl)-L-tryptophan + 5-(2-trans-butenyl)-L-tryptophan
-
?
2.5.1.34 additional information the enzyme catalyzes a Friedel-Crafts alkylation with high flexibility for aromatic substrates, but shows high specificity for dimethylallyl diphosphate. At least one methyl group in DMAPP can be deleted or shifted to the delta-position. For acceptance by some DMATS enzymes, however, a double bond must be situated at the beta-position. The alkylation position of an analogue can differ from that of dimethylallyl diphosphate. No activity with 3-methylbutanyl-diphosphate and 4-methyl-3-pentenyl-diphosphate. Product identification with NMR spectroscopy Aspergillus fumigatus ?
-
?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.B31 5-DMATS
-
Aspergillus clavatus
2.5.1.B31 C5-prenyltransferase
-
Aspergillus clavatus
2.5.1.B31 dimethylallyl-tryptophan synthase
-
Aspergillus clavatus
2.5.1.34 C4-prenyltransferase
-
Aspergillus fumigatus
2.5.1.34 dimethylallyl-tryptophan synthase
-
Aspergillus fumigatus
2.5.1.34 FgaPT2
-
Aspergillus fumigatus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.5.1.B31 37
-
assay at Aspergillus clavatus
2.5.1.34 37
-
assay at Aspergillus fumigatus

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.5.1.B31 0.005
-
methylallyl diphosphate 37°C, pH not specified in the publication Aspergillus clavatus
2.5.1.B31 0.023
-
2-pentenyl diphosphate 37°C, pH not specified in the publication Aspergillus clavatus
2.5.1.34 0.009
-
methylallyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus
2.5.1.34 0.011
-
2-pentenyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus

General Information

EC Number General Information Comment Organism
2.5.1.B31 evolution the enzyme belongs to the dimethylallyl-tryptophan synthase, DMATS, superfamily Aspergillus clavatus
2.5.1.34 evolution the enzyme belongs to the dimethylallyl-tryptophan synthase, DMATS, superfamily Aspergillus fumigatus

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.B31 0.136
-
methylallyl diphosphate 37°C, pH not specified in the publication Aspergillus clavatus
2.5.1.B31 0.174
-
2-pentenyl diphosphate 37°C, pH not specified in the publication Aspergillus clavatus
2.5.1.34 0.198
-
2-pentenyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus
2.5.1.34 0.232
-
methylallyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus