EC Number |
Substrates |
Organism |
Products |
Reversibility |
---|
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 |
the enzyme catalyzes the biosynthesis of the isocyanide-containing antibiotic(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate (i.e. L-tryptophan isonitrile) |
uncultured organism |
(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O |
- |
? |
4.1.99.25 | L-tryptophan + D-ribulose 5-phosphate |
the enzyme is involved in the biosynthetic pathways for vinyl isocyanides |
Xenorhabdus nematophila |
(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 |
Xenorhabdus nematophila |
(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 |
uncultured organism |
(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 |
- |
? |