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Literature summary extracted from

  • Mahmoodi, N.; Tanner, M.E.
    Potential rearrangements in the reaction catalyzed by the indole prenyltransferase FtmPT1 (2013), ChemBioChem, 14, 2029-2037.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.5.1.106 expressed in Escherichia coli Rosetta(DE3) pLysS cells Aspergillus fumigatus
2.5.1.106 expression in Escherichia coli Aspergillus fumigatus

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.106 Aspergillus fumigatus
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.5.1.106 Sepharose column chromatography, and gel filtration Aspergillus fumigatus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.106 dimethylallyl diphosphate + 2-methylbrevianamide F i.e. cyclo-L-2-methyltryptophan-L-proline Aspergillus fumigatus diphosphate + ?
-
 ?
2.5.1.106 dimethylallyl diphosphate + 5-hydroxybrevianamide F i.e. cyclo-L-5-hydroxytryptophan-L-proline Aspergillus fumigatus diphosphate + ?
-
 ?
2.5.1.106 dimethylallyl diphosphate + brevianamide F i.e. cyclo-L-Trp-L-Pro Aspergillus fumigatus diphosphate + tryprostatin B
-
 ?
2.5.1.106 dimethylallyl diphosphate + cyclo-L-2-methyltryptophan-L-proline i.e. 2-methylbrevianamide F Aspergillus fumigatus diphosphate + (5aS,6aS,13aS)-6a-(3-methylbut-2-en-1-yl)-2,3,6,6a,11,11a-hexahydro-1H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione product is a normal prenylated hexahydropyrroloindole that contains a substituent at C-3 and has cyclized. An N-1 normal prenylated product is formed as minor product ?
2.5.1.106 dimethylallyl diphosphate + L-tryptophan
-
 Aspergillus fumigatus diphosphate + ?
-
 ?
2.5.1.106 dimethylallyl diphosphate + L-tryptophan
-
 Aspergillus fumigatus diphosphate + (2S,3aR,8aR)-3a-(2-methylbut-3-en-2-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid 18% conversion after extended incubation, product is a hexahydropyrroloindole that results from reverse C-3 prenylation followed by ring closure ?
2.5.1.106 dimethylallylphosphate + cyclo-L-5-hydroxytryptophan-L-proline i.e. 5-hydroxybrevianamide F Aspergillus fumigatus diphosphate + (3S,8aS)-3-[[5-hydroxy-4-(3-methylbut-2-en-1-yl)-2,3-dihydro-1H-indol-3-yl]methyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione product is formed by normal prenylation in C-4 position ?
2.5.1.106 additional information a mechanism involving a C-3 normal prenylation as the first step of the catalysis. The barrier to the Cope rearrangement can be quite low, and it can readily proceed at room temperature in these biologically relevant systems. The slowest step in this nonenzymatic reaction might be ring opening of the hexahydropyrroloindole aminal Aspergillus fumigatus ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.106 FtmPT1
-
 Aspergillus fumigatus
2.5.1.106 indole prenyltransferase
-
 Aspergillus fumigatus