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2.5.1.106: tryprostatin B synthase

This is an abbreviated version!
For detailed information about tryprostatin B synthase, go to the full flat file.

Word Map on EC 2.5.1.106

Reaction

dimethylallyl diphosphate
+
brevianamide F
=
diphosphate
+
tryprostatin B

Synonyms

brevianamide F prenyltransferase, cyclic dipeptide C2-prenyltransferase FtmPT1, FtmPT1, indole prenyltransferase, tryprostatin B synthase

ECTree

     2 Transferases
         2.5 Transferring alkyl or aryl groups, other than methyl groups
             2.5.1 Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
                2.5.1.106 tryprostatin B synthase

Substrates Products

Substrates Products on EC 2.5.1.106 - tryprostatin B synthase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,6-dihydroxynaphthalene + dimethylallyl diphosphate
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalene-1,6-diol
show the reaction diagram
-
mutants Y205L, Y205M, Y205F, Y205C, Y205I, Y205S, and G115A_Y205C show higher catalytic activities than the non-mutated FtmPT1
-
-
?
1,7-dihydroxynaphthalene + dimethylallyl diphosphate
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalene-1,7-diol
show the reaction diagram
-
mutants Y205L, Y205M, Y205F, Y205C, Y205I, Y205S, and G115A_Y205C show higher catalytic activities than the non-mutated FtmPT1
-
-
?
1-amino-7-hydroxynaphthalene + dimethylallyl diphosphate
diphosphate + 8-amino-7-(3-methylbut-2-en-1-yl)naphthalen-2-ol
show the reaction diagram
-
mutants Y205L, Y205M, Y205F, Y205C, Y205I, Y205S, and G115A_Y205C show higher catalytic activities than the non-mutated FtmPT1
-
-
?
1-naphthol + dimethylallyl diphosphate
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalen-1-ol
show the reaction diagram
-
mutants Y205L, Y205M, Y205F, Y205C, Y205I, Y205S, and G115A_Y205C show higher catalytic activities than the non-mutated FtmPT1
-
-
?
2,3-dihydroxynaphthalene + dimethylallyl diphosphate
diphosphate + ?
show the reaction diagram
-
mutants Y205L, Y205M, Y205F, Y205C, Y205I, Y205S, and G115A_Y205C show higher catalytic activities than the non-mutated FtmPT1
-
-
?
2-naphthol + dimethylallyl diphosphate
diphosphate + ?
show the reaction diagram
-
mutants Y205L, Y205M, Y205F, Y205C, Y205I, Y205S, and G115A_Y205C show higher catalytic activities than the non-mutated FtmPT1
-
-
?
brevianamide F + dimethylallyl diphosphate
diphosphate + tryprostatin B
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + (E)-4-(1H-indol-3-yl)but-3-en-2-one
diphosphate + (3E)-3-(1H-indol-3-ylmethylidene)-6-methylhept-5-en-2-one
show the reaction diagram
dimethylallyl diphosphate + 2-methylbrevianamide F
diphosphate + ?
show the reaction diagram
-
i.e. cyclo-L-2-methyltryptophan-L-proline
-
-
?
dimethylallyl diphosphate + 5-hydroxybrevianamide F
diphosphate + ?
show the reaction diagram
-
i.e. cyclo-L-5-hydroxytryptophan-L-proline
-
-
?
dimethylallyl diphosphate + brevianamide F
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
show the reaction diagram
dimethylallyl diphosphate + brevianamide F
diphosphate + (5aS,6aR,11aR,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
show the reaction diagram
dimethylallyl diphosphate + brevianamide F
diphosphate + (5aS,6aR,11aS,13aS)-6a-(2-methylbut-3-en-2-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 + tryprostatin B
show the reaction diagram
the reaction occurs with mutant enzyme G115T
-
-
?
dimethylallyl diphosphate + brevianamide F
diphosphate + tryprostatin B
show the reaction diagram
dimethylallyl diphosphate + cyclo-(D-Trp-D-Ala)
diphosphate + cyclo-(D-2-dimethylallyl-Trp-D-Ala)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(D-Trp-D-Pro)
diphosphate + cyclo-(2-dimethylallyl-D-Trp-D-Pro)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(D-Trp-D-Pro)
diphosphate + cyclo-(D-2-dimethylallyl-Trp-D-Pro)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(D-Trp-L-Ala)
diphosphate + cyclo-(D-2-dimethylallyl-Trp-L-Ala)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(D-Trp-L-Pro)
diphosphate + cyclo-(2-dimethylallyl-D-Trp-L-Pro)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(D-Trp-L-Pro)
diphosphate + cyclo-(2-dimethylallyl-Trp-L-Pro)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(D-Trp-L-Pro)
diphosphate + cyclo-(D-2-dimethylallyl-Trp-L-Pro)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-D-Ala)
diphosphate + cyclo-(L-2-dimethylallyl-Trp-D-Ala)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-D-Pro)
diphosphate + cyclo-(2-dimethylallyl-L-Trp-D-Pro)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-D-Pro)
diphosphate + cyclo-(L-2-dimethylallyl-Trp-D-Pro)
show the reaction diagram
product yield 75.7%
-
-
?
dimethylallyl diphosphate + cyclo-(L-Trp-Gly)
diphosphate + cyclo-(L-2-dimethylallyl-Trp-Gly)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-L-Ala)
diphosphate + cyclo-(L-2-dimethylallyl-Trp-L-Ala)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-L-His)
diphosphate + cyclo-(L-2-dimethylallyl-Trp-L-His)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-L-Leu)
diphosphate + cyclo-(D-2-dimethylallyl-Trp-L-Leu)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-L-Phe)
diphosphate + cyclo-(L-2-dimethylallyl-Trp-L-Phe)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-L-Pro)
diphosphate + cyclo-(2-dimethylallyl-Trp-L-Pro)
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + cyclo-(L-Trp-L-Trp)
diphosphate + cyclo-(L-2-dimethylallyl-Trp-L-Trp)
show the reaction diagram
dimethylallyl diphosphate + cyclo-(L-Trp-L-Tyr)
diphosphate + cyclo-(L-2-dimethylallyl-Trp-L-Tyr)
show the reaction diagram
dimethylallyl diphosphate + cyclo-L-2-methyltryptophan-L-proline
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
show the reaction diagram
-
i.e. 2-methylbrevianamide F
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 + DL-4-methyl-tryptophan
diphosphate + DL-1-(3'-dimethylallyl)-4-methyl-tryptophan
show the reaction diagram
dimethylallyl diphosphate + DL-6-fluoro-tryptophan
diphosphate + DL-1-(3'-dimethylallyl)-6-fluoro-tryptophan
show the reaction diagram
dimethylallyl diphosphate + DL-6-methyl-tryptophan
diphosphate + DL-1-(3'-dimethylallyl)-6-methyl-tryptophan
show the reaction diagram
dimethylallyl diphosphate + DL-7-methyl-tryptophan
diphosphate + DL-1-(3'-dimethylallyl)-7-methyl-tryptophan
show the reaction diagram
-
conversion rate 24.3%
-
?
dimethylallyl diphosphate + L-Nalpha-methyl-tryptophan
diphosphate + L-1-(3'-dimethylallyl)-Nalpha-methyl-tryptophan
show the reaction diagram
-
conversion rate 11.1%
-
?
dimethylallyl diphosphate + L-tryptophan
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
show the reaction diagram
-
-
18% conversion after extended incubation, product is a hexahydropyrroloindole that results from reverse C-3 prenylation followed by ring closure
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + ?
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-1-(3'-dimethylallyl)-tryptophan
show the reaction diagram
-
conversion rate 37.8%
-
?
dimethylallylphosphate + cyclo-L-5-hydroxytryptophan-L-proline
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
show the reaction diagram
-
i.e. 5-hydroxybrevianamide F
product is formed by normal prenylation in C-4 position
-
?
additional information
?
-