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Literature summary extracted from

  • Hillwig, M.; Zhu, Q.; Liu, X.
    Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua (2014), ACS Chem. Biol., 9, 372-377 .
    View publication on PubMed

Application

EC Number Application Comment Organism
2.5.1.159 additional information the enzyme can be used as a versatile prenylation catalyst for the structural diversification of hapalindoles Fischerella ambigua

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.20.11 exprerssion in Escherichia coli Fischerella ambigua
4.1.99.25 overexpressed as N-His tagged protein in Escherichia coli Fischerella ambigua

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.20.11 (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + 2-oxoglutarate + O2 Fischerella ambigua
-
 3-[(Z)-2-isocyanoethenyl]-1H-indole + succinate + 2 CO2 + H2O
-
 ?
1.14.20.11 (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + 2-oxoglutarate + O2 Fischerella ambigua UTEX 1903
-
 3-[(Z)-2-isocyanoethenyl]-1H-indole + succinate + 2 CO2 + H2O
-
 ?
2.5.1.159 prenyl diphosphate + hapalindole G Fischerella ambigua
-
 ambiguine A + diphosphate
-
 ?
2.5.1.159 prenyl diphosphate + hapalindole G Fischerella ambigua UTEX1903
-
 ambiguine A + diphosphate
-
 ?
2.5.1.159 prenyl diphosphate + hapalindole U Fischerella ambigua
-
 ambiguine H + diphosphate
-
 ?
2.5.1.159 prenyl diphosphate + hapalindole U Fischerella ambigua UTEX1903
-
 ambiguine H + diphosphate
-
 ?
4.1.99.25 L-tryptophan + D-ribulose 5-phosphate Fischerella ambigua key enzyme in ambiguine biosynthesis (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?
4.1.99.25 L-tryptophan + D-ribulose 5-phosphate Fischerella ambigua UTEX1903 key enzyme in ambiguine biosynthesis (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.20.11 Fischerella ambigua V5TD18
-
-
1.14.20.11 Fischerella ambigua UTEX 1903 V5TD18
-
-
2.5.1.159 Fischerella ambigua
-
-
-
2.5.1.159 Fischerella ambigua UTEX1903
-
-
-
4.1.99.25 Fischerella ambigua V5TF65
-
-
4.1.99.25 Fischerella ambigua UTEX1903 V5TF65
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.1.99.25
-
 Fischerella ambigua

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.20.11 (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + 2-oxoglutarate + O2
-
 Fischerella ambigua 3-[(Z)-2-isocyanoethenyl]-1H-indole + succinate + 2 CO2 + H2O
-
 ?
1.14.20.11 (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + 2-oxoglutarate + O2
-
 Fischerella ambigua UTEX 1903 3-[(Z)-2-isocyanoethenyl]-1H-indole + succinate + 2 CO2 + H2O
-
 ?
2.5.1.159 dimethylallyl diphosphate + cis-indole nitrile
-
 Fischerella ambigua 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
-
 ?
2.5.1.159 dimethylallyl diphosphate + hapalindole A
-
 Fischerella ambigua 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
-
 ?
2.5.1.159 dimethylallyl diphosphate + hapalindole A
-
 Fischerella ambigua UTEX1903 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
-
 ?
2.5.1.159 geranyl diphosphate + cis-indole nitrile
-
 Fischerella ambigua 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
-
 ?
2.5.1.159 geranyl diphosphate + cis-indole nitrile
-
 Fischerella ambigua UTEX1903 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
-
 ?
2.5.1.159 additional information the enzyme does not accept L/D-Trp, trans/cis-1, or Trp-containing linear or cyclic dipeptide as substrates Fischerella ambigua ?
-
-
2.5.1.159 additional information the enzyme does not accept L/D-Trp, trans/cis-1, or Trp-containing linear or cyclic dipeptide as substrates Fischerella ambigua UTEX1903 ?
-
-
2.5.1.159 prenyl diphosphate + hapalindole G
-
 Fischerella ambigua ambiguine A + diphosphate
-
 ?
2.5.1.159 prenyl diphosphate + hapalindole G
-
 Fischerella ambigua UTEX1903 ambiguine A + diphosphate
-
 ?
2.5.1.159 prenyl diphosphate + hapalindole U
-
 Fischerella ambigua ambiguine H + diphosphate
-
 ?
2.5.1.159 prenyl diphosphate + hapalindole U
-
 Fischerella ambigua UTEX1903 ambiguine H + diphosphate
-
 ?
4.1.99.25 L-tryptophan + D-ribulose 5-phosphate key enzyme in ambiguine biosynthesis Fischerella ambigua (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?
4.1.99.25 L-tryptophan + D-ribulose 5-phosphate (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate i.e. L-tryptophan isonitrile, hydroxyacetone i.e. 1-hydroxypropan-2-one. According to the proposed mechanism, the enzyme forms an imine intermediate composed of linked L-tryptophan and D-ribulose 5-phosphate, followed by loss of the phosphate group and formation of a beta-keto imine and keto-enol tautomerization. This is followed by a C-C bond cleavage, the release of hydroxyacetone, and a retro aldol type reaction that releases formaldehyde and forms the final product Fischerella ambigua (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?
4.1.99.25 L-tryptophan + D-ribulose 5-phosphate key enzyme in ambiguine biosynthesis Fischerella ambigua UTEX1903 (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?
4.1.99.25 L-tryptophan + D-ribulose 5-phosphate (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate i.e. L-tryptophan isonitrile, hydroxyacetone i.e. 1-hydroxypropan-2-one. According to the proposed mechanism, the enzyme forms an imine intermediate composed of linked L-tryptophan and D-ribulose 5-phosphate, followed by loss of the phosphate group and formation of a beta-keto imine and keto-enol tautomerization. This is followed by a C-C bond cleavage, the release of hydroxyacetone, and a retro aldol type reaction that releases formaldehyde and forms the final product Fischerella ambigua UTEX1903 (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.20.11 ambI3
-
 Fischerella ambigua
1.14.20.11 famH3
-
 Fischerella ambigua
2.5.1.159 ambP3
-
 Fischerella ambigua

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.5.1.159 0.088
-
 hapalindole G pH and temperature not specified in the publication Fischerella ambigua

General Information

EC Number General Information Comment Organism
1.14.20.11 physiological function presence of isonitrile synthase AmbI1 and AmbI3 alone are sufficient to generate 3-[(Z)-2-isocyanoethenyl]-1H-indole from L-Trp and ribulose 5-phosphate Fischerella ambigua
4.1.99.25 metabolism key enzyme in ambiguine biosynthesis Fischerella ambigua