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Literature summary for 4.1.99.25 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
Search for more literature for 4.1.99.25

Cloned(Commentary)

Cloned (Comment) Organism
overexpressed as N-His tagged protein in Escherichia coli Fischerella ambigua

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
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
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 ?
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
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 ?

Organism

Organism UniProt Comment Textmining
Fischerella ambigua V5TF65
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Fischerella ambigua UTEX1903 V5TF65
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Purification (Commentary)

Purification (Comment) Organism
-
 Fischerella ambigua

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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
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 ?
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
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 ?
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
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 ?
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
-
 ?

General Information

General Information Comment Organism
metabolism key enzyme in ambiguine biosynthesis Fischerella ambigua