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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

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
-
 ?
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
-
-
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
-
 ?
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

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