EC 1.14.20.11 - 3-[(Z)-2-isocyanoethenyl]-1H-indole synthase

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IntEnz Enzyme Nomenclature
EC 1.14.20.11

Names

Accepted name:
3-[(Z)-2-isocyanoethenyl]-1H-indole synthase
Other names:
ambI3 (gene name)
famH3 (gene name)
Systematic name:
(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate,2-oxoglutarate:oxygen oxidoreductase (decarboxylating, 3-[(Z)-2-isocyanoethenyl]-1H-indole-forming)

Reaction

Comments:

The enzyme, characterized from the cyanobacterium Fischerella ambigua UTEX 1903, participates in the biosynthesis of hapalindole-type alkaloids. The enzyme catalyses an Fe2+, 2-oxoglutarate-dependent monooxygenation at C-3, which is followed by decarboxylation and dehydration, resulting in the generation of a cis C-C double bond. cf. EC 1.14.20.12, L-tryptophan isonitrile desaturase/decarboxylase (3-[(E)-2-isocyanoethenyl]-1H-indole-forming).

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB

References

  1. Hillwig, M. L., Zhu, Q., Liu, X.
    Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua.
    ACS Chem. Biol. 9 : 372-377 (2014). [PMID: 24180436]
  2. Chang, W. C., Sanyal, D., Huang, J. L., Ittiamornkul, K., Zhu, Q., Liu, X.
    In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate.
    Org. Lett. 19 : 1208-1211 (2017). [PMID: 28212039]

[EC 1.14.20.11 created 2018]