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ENZYME entry: EC 4.1.99.25

Accepted Name
L-tryptophan isonitrile synthase.
Reaction catalysed
L-tryptophan + D-ribulose 5-phosphate <=> (2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H(2)O
Comment(s)
  • The enzymes from cyanobacteria that belong to the Stigonematales 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 acetol, and a retro aldol type reaction that releases formaldehyde and forms the final product.
  • Cf. EC 4.1.99.24, L-tyrosine isonitrile synthase.
Cross-references
BRENDA4.1.99.25
EC2PDB4.1.99.25
ExplorEnz4.1.99.25
PRIAM enzyme-specific profiles4.1.99.25
KEGG Ligand Database for Enzyme Nomenclature4.1.99.25
IUBMB Enzyme Nomenclature4.1.99.25
IntEnz4.1.99.25
MEDLINEFind literature relating to 4.1.99.25
MetaCyc4.1.99.25

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