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Literature summary for 2.5.1.106 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
Search for more literature for 2.5.1.106

Cloned(Commentary)

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

Organism

Organism UniProt Comment Textmining
Aspergillus fumigatus
-
-
-

Purification (Commentary)

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
dimethylallyl diphosphate + 2-methylbrevianamide F i.e. cyclo-L-2-methyltryptophan-L-proline Aspergillus fumigatus diphosphate + ?
-
 ?
dimethylallyl diphosphate + 5-hydroxybrevianamide F i.e. cyclo-L-5-hydroxytryptophan-L-proline Aspergillus fumigatus diphosphate + ?
-
 ?
dimethylallyl diphosphate + brevianamide F i.e. cyclo-L-Trp-L-Pro Aspergillus fumigatus diphosphate + tryprostatin B
-
 ?
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 ?
dimethylallyl diphosphate + L-tryptophan
-
 Aspergillus fumigatus diphosphate + ?
-
 ?
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 ?
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 ?
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

Synonyms Comment Organism
FtmPT1
-
 Aspergillus fumigatus
indole prenyltransferase
-
 Aspergillus fumigatus