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Information on EC 2.5.1.159 - hapalindole G dimethylallyltransferase
for references in articles please use BRENDA:EC2.5.1.159
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EC Tree 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)
2.5.1.159 hapalindole G dimethylallyltransferase
IUBMB Comments
Requires Mg2+. The enzyme, characterized from the cyanobacterium Fischerella ambigua UTEX 1903, is involved in the biosynthesis of hapalindole-type alkaloids.
The expected taxonomic range for this enzyme is: Fischerella ambigua
Reaction Schemes
showSynonyms
ambP3, FamD1, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ambP3
FamD1
ambP3
-
-
-
-
FamD1
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
prenyl diphosphate + hapalindole G = ambiguine A + diphosphate
(1)
-
-
-
prenyl diphosphate + hapalindole U = ambiguine H + diphosphate
(2)
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
prenyl-diphosphate:hapalindole G prenyltransferase (ambiguine A-forming)
Requires Mg2+. The enzyme, characterized from the cyanobacterium Fischerella ambigua UTEX 1903, is involved in the biosynthesis of hapalindole-type alkaloids.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + cis-indole nitrile
3-[(Z)-2-isocyanoethenyl]-2-(3-methylbut-2-en-1-yl)-1H-indole + 3-[(Z)-2-isocyanoethenyl]-3-(3-methylbut-2-en-1-yl)-3H-indole + diphosphate
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
geranyl diphosphate + cis-indole nitrile
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-1H-indole + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-3H-indole + diphosphate
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole G
ambiguine A + diphosphate
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole G
ambiguine A + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole G
ambiguine A + diphosphate
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole G
ambiguine A + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole U
ambiguine H + diphosphate
A0A1J0AKI6
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole U
ambiguine H + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole U
ambiguine H + diphosphate
A0A1J0AKI6
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole U
ambiguine H + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + cis-indole nitrile
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-1H-indole + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-3H-indole + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + cis-indole nitrile
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-1H-indole + 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-[(Z)-2-isocyanoethenyl]-3H-indole + diphosphate
-
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole G
ambiguine A + diphosphate
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole G
ambiguine A + diphosphate
-
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole G
ambiguine A + diphosphate
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole G
ambiguine A + diphosphate
-
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole U
ambiguine H + diphosphate
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole U
ambiguine H + diphosphate
-
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole U
ambiguine H + diphosphate
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole U
ambiguine H + diphosphate
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: the enzyme does not accept indole substrates without bicyclic terpenoid rings, including l/d-Trp, trans/cisindolyl vinyl isonitrile, and Trp-containing dipeptides
Products: -
Products: -
-
additional information
?
-
-
Substrates: the enzyme does not accept L/D-Trp, trans/cis-1, or Trp-containing linear or cyclic dipeptide as substrates
Products: -
Products: -
-
additional information
?
-
Substrates: the enzyme does not accept indole substrates without bicyclic terpenoid rings, including l/d-Trp, trans/cisindolyl vinyl isonitrile, and Trp-containing dipeptides
Products: -
Products: -
-
additional information
?
-
-
Substrates: the enzyme does not accept L/D-Trp, trans/cis-1, or Trp-containing linear or cyclic dipeptide as substrates
Products: -
Products: -
-
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole A
6aS,8R,9R,10R,10aR)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-1-(3-methylbut-2-en-1-yl)-2,6,6a,7,8,9,10,10a-octahydronaphtho[1,2,3-cd]indole + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole G
ambiguine A + diphosphate
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole G
ambiguine A + diphosphate
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole U
ambiguine H + diphosphate
A0A1J0AKI6
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + hapalindole U
ambiguine H + diphosphate
A0A1J0AKI6
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole G
ambiguine A + diphosphate
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole G
ambiguine A + diphosphate
-
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole G
ambiguine A + diphosphate
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole G
ambiguine A + diphosphate
-
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole U
ambiguine H + diphosphate
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole U
ambiguine H + diphosphate
-
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole U
ambiguine H + diphosphate
Substrates: -
Products: -
Products: -
?
prenyl diphosphate + hapalindole U
ambiguine H + diphosphate
-
Substrates: -
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.088
hapalindole G
-
pH and temperature not specified in the publication
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). AMBP3_FISAU
Fischerella ambigua (strain UTEX 1903)
322
0
36479
Swiss-Prot
other Location (Reliability: 1)
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
native enzyme and enzyme in complex with cis-indole nitrile and/or dimethylallyl S-thiolodiphosphate, hanging drop vapor diffusion method, using 1.0 M sodium citrate, 0.1 M imidazole, pH 8.0
A0A1J0AKI6
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
W117Y
the mutant retains activity (94% for hapalindole U and 74% for hapalindole A compared to the wild type enzyme)
W117Y
-
the mutant retains activity (94% for hapalindole U and 74% for hapalindole A compared to the wild type enzyme)
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
the enzyme can be used as a versatile prenylation catalyst for the structural diversification of hapalindoles
additional information
-
the enzyme can be used as a versatile prenylation catalyst for the structural diversification of hapalindoles
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hillwig, M.; Zhu, Q.; Liu, X.
Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua
ACS Chem. Biol.
9
372-377
2014
Fischerella ambigua, Fischerella ambigua UTEX1903
brenda
Wang, J.; Chen, C.C.; Yang, Y.; Liu, W.; Ko, T.P.; Shang, N.; Hu, X.; Xie, Y.; Huang, J.W.; Zhang, Y.; Guo, R.T.
Structural insight into a novel indole prenyltransferase in hapalindole-type alkaloid biosynthesis
Biochem. Biophys. Res. Commun.
495
1782-1788
2018
Fischerella ambigua (A0A1J0AKI6), Fischerella ambigua UTEX 1903 (A0A1J0AKI6)
brenda
Wong, C.P.; Awakawa, T.; Nakashima, Y.; Mori, T.; Zhu, Q.; Liu, X.; Abe, I.
Two distinct substrate binding modes for the normal and reverse prenylation of hapalindoles by the prenyltransferase AmbP3
Angew. Chem. Int. Ed. Engl.
57
560-563
2018
Fischerella ambigua (V5TDY7), Fischerella ambigua UTEX1903 (V5TDY7)
brenda
Awakawa, T.; Abe, I.
Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis
Beilstein J. Org. Chem.
15
1545-1551
2019
Fischerella ambigua (V5TDY7), Fischerella ambigua UTEX 1903 (V5TDY7)
brenda
Micallef, M.; Sharma, D.; Bunn, B.; Gerwick, L.; Viswanathan, R.; Moffitt, M.
Comparative analysis of hapalindole, ambiguine and welwitindolinone gene clusters and reconstitution of indole-isonitrile biosynthesis from cyanobacteria
BMC Microbiol.
14
213
2014
Fischerella ambigua, Fischerella ambigua UTEX 1903
brenda
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