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Literature summary extracted from

  • Fan, A.; Winkelblech, J.; Li, S.M.
    Impacts and perspectives of prenyltransferases of the DMATS superfamily for use in biotechnology (2015), Appl. Microbiol. Biotechnol., 99, 7399-7415.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.5.1.80 recombinant enzyme overexpression Aspergillus fumigatus

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.5.1.34 crystal structure analysis Aspergillus fumigatus

Protein Variants

EC Number Protein Variants Comment Organism
2.5.1.34 K174A site.directed mutagenesis, the mutant FgaPT2 converts tryptophan mainly to a reversely C3-prenylated derivative, while the regularly C4-prenylated tryptophan is detected as a minor product Aspergillus fumigatus
2.5.1.34 additional information molecular modeling-guided site-directed mutagenesis of FgaPT2. FgaPT2 is displayed on the surface of Escherichia coli cells by using autodisplay technique for chemoenzymatic synthesis. Indole-3-propionic acid and L-beta-homotryptophan are tested with the FgaPT2 whole cell biocatalyst, and conversion yields of 30 and 13% are obtained, respectively. Its catalytic efficiency is much higher than that of the purified FgaPT2 in a 24-h assay toward indole-3-propionic acid, overview Aspergillus fumigatus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.34 dimethylallyl diphosphate + L-tryptophan Aspergillus fumigatus C-4 prenylation diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + L-tryptophan Aspergillus fumigatus
-
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.34 Aspergillus fumigatus Q50EL0
-
-
2.5.1.80 Aspergillus fumigatus Q4WYG3 gene 7-DMATS
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.5.1.80 recombinant enzyme Aspergillus fumigatus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.34 2-pentenyl diphosphate + L-tryptophan C-5 prenylation Aspergillus fumigatus diphosphate + 5-(pent-2-enyl)-L-tryptophan
-
?
2.5.1.34 benzyl diphosphate + L-tryptophan C-5 prenylation Aspergillus fumigatus diphosphate + 5-benzyl-L-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + 11-methyl-DL-tryptophan 1.6% of the activity with L-Trp Aspergillus fumigatus diphosphate + 11-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + 4-amino-L-Phe C-3 prenylation Aspergillus fumigatus diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-Phe
-
?
2.5.1.34 dimethylallyl diphosphate + 5-hydroxy-L-tryptophan 21.0% of the activity with L-Trp Aspergillus fumigatus diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + 5-methyl-DL-tryptophan 8.1% of the activity with L-Trp Aspergillus fumigatus diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + 6-methyl-DL-tryptophan 15.2% of the activity with L-Trp Aspergillus fumigatus diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + 7-methyl-DL-tryptophan 16.3% of the activity with L-Trp Aspergillus fumigatus diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + beta-homo-L-tryptophan 51.5% of the activity with L-Trp Aspergillus fumigatus ?
-
?
2.5.1.34 dimethylallyl diphosphate + cyclo-L-Trp-Gly
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
-
?
2.5.1.34 dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
-
?
2.5.1.34 dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
-
?
2.5.1.34 dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
?
2.5.1.34 dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
-
Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
-
?
2.5.1.34 dimethylallyl diphosphate + D-tryptophan 9.7% of the activity with L-Trp Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + DL-indole-3-lactic acid 10.5% of the activity with L-Trp Aspergillus fumigatus ?
-
?
2.5.1.34 dimethylallyl diphosphate + indole-3-propionic acid 32.2% of the activity with L-Trp Aspergillus fumigatus ?
-
?
2.5.1.34 dimethylallyl diphosphate + L-abrine 58.0% of the activity with L-Trp Aspergillus fumigatus ?
-
?
2.5.1.34 dimethylallyl diphosphate + L-tryptophan best substrate Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + L-tryptophan C-4 prenylation Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.34 dimethylallyl diphosphate + L-Tyr C-3 prenylation Aspergillus fumigatus diphosphate + 3-(3-methylbut-2-enyl)-L-Tyr 3-dimethylallyl-L-tyrosine ?
2.5.1.34 methylallyl diphosphate + L-tryptophan C-4 and C-5 prenylation Aspergillus fumigatus diphosphate + 4-(but-2-enyl)-L-tryptophan
-
?
2.5.1.34 methylallyl diphosphate + L-tryptophan C-4 and C-5 prenylation Aspergillus fumigatus diphosphate + 5-(but-2-enyl)-L-tryptophan
-
?
2.5.1.34 additional information no or poor activity with N-acetyl-DL-Trp, 5-bromo-DL-Trp, 4-methyl-DL-Trp, 1-methyl-DL-Trp, and 6-fluoro-DL-Trp. The tryptophan prenyltransferase FgaPT2 takes L-tyrosine and 4-amino-L-phenylalanine as substrates as well and produces the unique C3-prenylated tyrosine or 4-amino-L-phenylalanine, cf. EC 2.5.1.122, no activity with D-Tyr, 3-fluoro-DL-Tyr, 3-iodo-L-Tyr, and alpha-methyl-L-Tyr. FgaPT2 also catalyzes regiospecific prenylations of indolocarbazoles at the para-position of the indole N-atom. In the presence of methylallyl diphosphate, MAPP, a mixture of C4- and C5-alkylated tryptophan is observed for FgaPT2 reaction,t FgaPT2 even uses the more space-demanding substrate benzyl diphosphate as donor and produces regiospecifically C5-benzylated tryptophan and eight derivatives thereof, overview Aspergillus fumigatus ?
-
?
2.5.1.80 2-pentenyl diphosphate + L-tryptophan C-5 prenylation Aspergillus fumigatus diphosphate + 5-(pent-2-enyl)-L-tryptophan
-
?
2.5.1.80 benzyl diphosphate + L-tryptophan C-5 prenylation Aspergillus fumigatus diphosphate + 5-benzyl-L-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 1-methyl-DL-tryptophan
-
Aspergillus fumigatus diphosphate + 1-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 11-methyl-DL-tryptophan
-
Aspergillus fumigatus diphosphate + 11-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 3-iodo-L-tyrosine C-4 prenylation Aspergillus fumigatus diphosphate + 3-iodo-4-(3-methylbut-2-enyl)-L-tyrosine
-
?
2.5.1.80 dimethylallyl diphosphate + 4-amino-L-phenylalanine C-4 prenylation Aspergillus fumigatus diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-phenylalanine
-
?
2.5.1.80 dimethylallyl diphosphate + 4-methyl-DL-tryptophan
-
Aspergillus fumigatus diphosphate + 4-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 5-bromo-L-tryptophan low activity Aspergillus fumigatus diphosphate + 5-bromo-4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
-
Aspergillus fumigatus diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 5-methyl-DL-tryptophan
-
Aspergillus fumigatus diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
-
Aspergillus fumigatus diphosphate + 6-fluoro-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + 6-methyl-DL-tryptophan low activity Aspergillus fumigatus diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + beta-homo-L-tryptophan
-
Aspergillus fumigatus ?
-
?
2.5.1.80 dimethylallyl diphosphate + D-tryptophan low activity Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + DL-indole-3-lactic acid
-
Aspergillus fumigatus ?
-
?
2.5.1.80 dimethylallyl diphosphate + indole-3-propionic acid
-
Aspergillus fumigatus ?
-
?
2.5.1.80 dimethylallyl diphosphate + L-abrine
-
Aspergillus fumigatus ?
-
?
2.5.1.80 dimethylallyl diphosphate + L-o-tyrosine C-4 prenylation Aspergillus fumigatus diphosphate + 4-(3-methylbut-2-enyl)-L-o-tyrosine 4-dimethylallyl-L-o-tyrosine ?
2.5.1.80 dimethylallyl diphosphate + L-tryptophan
-
Aspergillus fumigatus diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
?
2.5.1.80 dimethylallyl diphosphate + N-acetyl-DL-tryptophan
-
Aspergillus fumigatus diphosphate + N-acetyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
?
2.5.1.80 methylallyl diphosphate + L-tryptophan C-4 and C-5 prenylation Aspergillus fumigatus diphosphate + 4-(but-2-enyl)-L-tryptophan
-
?
2.5.1.80 methylallyl diphosphate + L-tryptophan C-4 and C-5 prenylation Aspergillus fumigatus diphosphate + 5-(but-2-enyl)-L-tryptophan
-
?
2.5.1.80 additional information no activity with 7-methyl-DL-tryptophan, alpha-methyl-L-tyrosine, L-m-tyrosine, and D-tyrosine. The enzyme is also active with hydroxynaphthalenes which it prenylates at C-4 or C-1, overview Aspergillus fumigatus ?
-
?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.34 FgaPT2
-
Aspergillus fumigatus
2.5.1.34 tryptophan C4-PT
-
Aspergillus fumigatus
2.5.1.80 7-DMATS
-
Aspergillus fumigatus

General Information

EC Number General Information Comment Organism
2.5.1.34 evolution the enzyme is part of the DMATS superfamily Aspergillus fumigatus
2.5.1.80 evolution the enzyme is part of the DMATS superfamily Aspergillus fumigatus