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Literature summary for 2.5.1.106 extracted from

  • Wollinsky, B.; Ludwig, L.; Xie, X.; Li, S.M.
    Breaking the regioselectivity of indole prenyltransferases: identification of regular C3-prenylated hexahydropyrrolo[2,3-b]indoles as side products of the regular C2-prenyltransferase FtmPT1 (2012), Org. Biomol. Chem., 10, 9262-9270.
    View publication on PubMed
Search for more literature for 2.5.1.106

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.14
-
 cyclo-(D-Trp-D-Pro) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.14
-
 cyclo-(D-Trp-L-Ala) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.16
-
 brevianamide F pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.27
-
 cyclo-(L-Trp-L-Tyr) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.37
-
 cyclo-(L-Trp-L-Tyr) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.39
-
 cyclo-(D-Trp-L-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.41
-
 cyclo-(L-Trp-D-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.45
-
 cyclo-(L-Trp-L-His) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.48
-
 cyclo-(L-Trp-L-Ala) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.54
-
 cyclo-(L-Trp-L-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.69
-
 cyclo-(L-Trp-Gly) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.77
-
 cyclo-(L-Trp-Gly) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus

Organism

Organism UniProt Comment Textmining
Aspergillus fumigatus Q4WAW7
-
-
Aspergillus fumigatus Af293 Q4WAW7
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dimethylallyl diphosphate + brevianamide F i.e. cyclo-(L-Trp-L-Pro) Aspergillus fumigatus diphosphate + tryprostatin B 82.3% yield of C2-prenylated product, plus 0.7% C3-prenylated product ?
dimethylallyl diphosphate + brevianamide F i.e. cyclo-(L-Trp-L-Pro) Aspergillus fumigatus Af293 diphosphate + tryprostatin B 82.3% yield of C2-prenylated product, plus 0.7% C3-prenylated product ?
dimethylallyl diphosphate + cyclo-(D-Trp-D-Pro) 43.4% yield of C2-prenylated product, plus 11.8% C3-prenylated product Aspergillus fumigatus diphosphate + cyclo-(D-2-dimethylallyl-Trp-D-Pro)
-
 ?
dimethylallyl diphosphate + cyclo-(D-Trp-D-Pro) 43.4% yield of C2-prenylated product, plus 11.8% C3-prenylated product Aspergillus fumigatus Af293 diphosphate + cyclo-(D-2-dimethylallyl-Trp-D-Pro)
-
 ?
dimethylallyl diphosphate + cyclo-(D-Trp-L-Ala) 46.4% yield of C2-prenylated product, plus 11.6% C3-prenylated product Aspergillus fumigatus diphosphate + cyclo-(D-2-dimethylallyl-Trp-L-Ala)
-
 ?
dimethylallyl diphosphate + cyclo-(D-Trp-L-Ala) 46.4% yield of C2-prenylated product, plus 11.6% C3-prenylated product Aspergillus fumigatus Af293 diphosphate + cyclo-(D-2-dimethylallyl-Trp-L-Ala)
-
 ?
dimethylallyl diphosphate + cyclo-(L-Trp-D-Ala) 43.9% yield of C2-prenylated product, plus 12.1% C3-prenylated product Aspergillus fumigatus diphosphate + cyclo-(L-2-dimethylallyl-Trp-D-Ala)
-
 ?
dimethylallyl diphosphate + cyclo-(L-Trp-D-Ala) 43.9% yield of C2-prenylated product, plus 12.1% C3-prenylated product Aspergillus fumigatus Af293 diphosphate + cyclo-(L-2-dimethylallyl-Trp-D-Ala)
-
 ?
dimethylallyl diphosphate + cyclo-(L-Trp-Gly) 57% yield of C2-prenylated product, plus 18.6% C3-prenylated product Aspergillus fumigatus diphosphate + cyclo-(L-2-dimethylallyl-Trp-Gly)
-
 ?
dimethylallyl diphosphate + cyclo-(L-Trp-L-Ala) 53.5% yield of C2-prenylated product, plus 12.7% C3-prenylated product Aspergillus fumigatus diphosphate + cyclo-(L-2-dimethylallyl-Trp-L-Ala)
-
 ?
dimethylallyl diphosphate + cyclo-(L-Trp-L-His) 68.1% yield of C2-prenylated product, plus 6.8% C3-prenylated product Aspergillus fumigatus diphosphate + cyclo-(L-2-dimethylallyl-Trp-L-His)
-
 ?
dimethylallyl diphosphate + cyclo-(L-Trp-L-Tyr) 72.4% yield of C2-prenylated product, plus 1.1% C3-prenylated product Aspergillus fumigatus diphosphate + cyclo-(L-2-dimethylallyl-Trp-L-Tyr)
-
 ?
additional information enzyme catalyzes also regular C3-prenylation as side reaction. Prenylation products at C2 and C3 are independently formed during the enzyme reaction. Both C2- and C3-prenylations may begin simultaneously with the attack of the electron-rich indole ring at C2 and C33 to C1' of the dimethylallyl cation. Their ratio would be dependent on the position of a given aromatic substrate and accordingly the distance of C2 to C1' as well as C3 to C1' Aspergillus fumigatus ?
-
 ?
additional information enzyme catalyzes also regular C3-prenylation as side reaction. Prenylation products at C2 and C3 are independently formed during the enzyme reaction. Both C2- and C3-prenylations may begin simultaneously with the attack of the electron-rich indole ring at C2 and C33 to C1' of the dimethylallyl cation. Their ratio would be dependent on the position of a given aromatic substrate and accordingly the distance of C2 to C1' as well as C3 to C1' Aspergillus fumigatus Af293 ?
-
 ?

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.06
-
 cyclo-(D-Trp-L-Ala) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.09
-
 cyclo-(L-Trp-L-Tyr) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.13
-
 cyclo-(L-Trp-L-Ala) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.24
-
 cyclo-(D-Trp-L-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.31
-
 cyclo-(D-Trp-D-Pro) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
0.71
-
 cyclo-(L-Trp-D-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
1.47
-
 cyclo-(L-Trp-L-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
1.73
-
 cyclo-(L-Trp-L-Tyr) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
2.55
-
 cyclo-(L-Trp-Gly) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
3.14
-
 cyclo-(L-Trp-Gly) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
4.05
-
 brevianamide F pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
21.14
-
 cyclo-(L-Trp-L-His) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.25
-
 cyclo-(L-Trp-L-Tyr) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.27
-
 cyclo-(L-Trp-L-Ala) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.43
-
 cyclo-(D-Trp-L-Ala) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
0.61
-
 cyclo-(D-Trp-L-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
1.73
-
 cyclo-(L-Trp-D-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
2.21
-
 cyclo-(D-Trp-D-Pro) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
2.72
-
 cyclo-(L-Trp-L-Ala) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
3.69
-
 cyclo-(L-Trp-Gly) pH 7.5, 37°C, prenylation at C3 Aspergillus fumigatus
4.08
-
 cyclo-(L-Trp-Gly) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
4.76
-
 cyclo-(L-Trp-L-His) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
6.41
-
 cyclo-(L-Trp-L-Tyr) pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus
25.3
-
 brevianamide F pH 7.5, 37°C, prenylation at C2 Aspergillus fumigatus