KEGG ENZYME: 1.14.20.11

ENZYME: 1.14.20.11

Entry

EC 1.14.20.11               Enzyme

Name

3-[(Z)-2-isocyanoethenyl]-1H-indole synthase;
ambI3 (gene name);
famH3 (gene name);
L-tryptophan isonitrile desaturase/decarboxylase (3-[(Z)-2-isocyanoethenyl]-1H-indole-forming)

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and the other dehydrogenated

Sysname

(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate,2-oxoglutarate:oxygen oxidoreductase (decarboxylating, 3-[(Z)-2-isocyanoethenyl]-1H-indole-forming)

Reaction(IUBMB)

(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate + 2-oxoglutarate + O2 = 3-[(Z)-2-isocyanoethenyl]-1H-indole + succinate + 2 CO2 + H2O [RN:R12082]

Reaction(KEGG)

R12082

Substrate

(2S)-3-(1H-indol-3-yl)-2-isocyanopropanoate [CPD:C21892];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]

Product

3-[(Z)-2-isocyanoethenyl]-1H-indole [CPD:C21893];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001]

Comment

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, 3-[(E)-2-isocyanoethenyl]-1H-indole synthase.

History

EC 1.14.20.11 created 2018

Orthology

K22876

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

Reference

1 [PMID:24180436]

Authors

Hillwig ML, Zhu Q, Liu X

Title

Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua.

Journal