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Literature summary extracted from

  • Chang, W.; Sanyal, D.; Huang, J.; Ittiamornkul, K.; Zhu, Q.; Liu, X.
    In vitro stepwise reconstitution of amino acid derived vinyl isocyanide biosynthesis detection of an elusive intermediate (2017), Org. Lett., 19, 1208-1211 .
    View publication on PubMed

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.1.99.24 L-tyrosine + D-ribulose 5-phosphate Xenorhabdus nematophila
-
 (2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?
4.1.99.25 L-tryptophan + D-ribulose 5-phosphate Xenorhabdus nematophila the enzyme is involved in the biosynthetic pathways for vinyl isocyanides (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.1.99.24 Xenorhabdus nematophila
-
-
-
4.1.99.25 Xenorhabdus nematophila D3V9Q4
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.1.99.24 L-tyrosine + D-ribulose 5-phosphate
-
 Xenorhabdus nematophila (2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
-
 ?
4.1.99.24 L-tyrosine + D-ribulose 5-phosphate according to the proposed mechanism, the enzyme forms an imine intermediate composed of linked L-tyrosine 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 Xenorhabdus nematophila (2S)-3-(4-hydroxyphenyl)-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
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.1.99.24 pvcA
-
 Xenorhabdus nematophila
4.1.99.25 isnA
-
 Xenorhabdus nematophila

General Information

EC Number General Information Comment Organism
4.1.99.24 metabolism the enzyme is involved in the biosynthetic pathways for vinyl isocyanides Xenorhabdus nematophila
4.1.99.25 metabolism the enzyme is involved in the biosynthetic pathways for vinyl isocyanides Xenorhabdus nematophila