Information on EC - L-tryptophan isonitrile synthase

for references in articles please use BRENDA:EC4.1.99.25
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EC Tree
     4 Lyases
         4.1 Carbon-carbon lyases
             4.1.99 Other carbon-carbon lyases
       L-tryptophan isonitrile synthase
IUBMB Comments
The enzymes from cyanobacteria that belong to the Nostocales order participate in the biosynthesis of hapalindole-type alkaloids. 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 . cf. EC, L-tyrosine isonitrile synthase.
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The enzyme appears in viruses and cellular organisms
ambI1, isnA, well1, more
L-tryptophan + D-ribulose 5-phosphate = (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O
show the reaction diagram
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