KEGG   ENZYME: 1.14.20.11Help
Entry
EC 1.14.20.11               Enzyme                                 

Name
3-[(Z)-2-isocyanoethenyl]-1H-indole synthase;
ambI3 (gene name);
famH3 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and the other dehydrogenated
BRITE hierarchy
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)
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, L-tryptophan isonitrile desaturase/decarboxylase (3-[(E)-2-isocyanoethenyl]-1H-indole-forming).
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
ACS Chem Biol 9:372-7 (2014)
DOI:10.1021/cb400681n
  Sequence
Reference
2  [PMID:28212039]
  Authors
Chang WC, Sanyal D, Huang JL, Ittiamornkul K, Zhu Q, Liu X
  Title
In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate.
  Journal
Org Lett 19:1208-1211 (2017)
DOI:10.1021/acs.orglett.7b00258
Other DBs
ExplorEnz - The Enzyme Database: 1.14.20.11
IUBMB Enzyme Nomenclature: 1.14.20.11
ExPASy - ENZYME nomenclature database: 1.14.20.11
BRENDA, the Enzyme Database: 1.14.20.11

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