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Literature summary for 2.5.1.34 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

Application Comment Organism
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]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.04
-
methylallyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus
0.056
-
2-pentenyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
dimethylallyl diphosphate + L-tryptophan Aspergillus fumigatus
-
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?

Organism

Organism UniProt Comment Textmining
Aspergillus fumigatus
-
-
-

Reaction

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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
-
?
dimethylallyl diphosphate + L-tryptophan
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan dimethylallyl diphosphate is the preferred substrate Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
methylallyl diphosphate + L-tryptophan very low activity Aspergillus fumigatus diphosphate + 4-(2-trans-butenyl)-L-tryptophan + 5-(2-trans-butenyl)-L-tryptophan
-
?
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

Synonyms Comment Organism
C4-prenyltransferase
-
Aspergillus fumigatus
dimethylallyl-tryptophan synthase
-
Aspergillus fumigatus
FgaPT2
-
Aspergillus fumigatus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Aspergillus fumigatus

Turnover Number [1/s]

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

General Information

General Information Comment Organism
evolution the enzyme belongs to the dimethylallyl-tryptophan synthase, DMATS, superfamily Aspergillus fumigatus

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.198
-
2-pentenyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus
0.232
-
methylallyl diphosphate 37°C, pH not specified in the publication Aspergillus fumigatus