KEGG   ENZYME: 1.14.20.14Help
Entry
EC 1.14.20.14               Enzyme                                 

Name
hapalindole-type alkaloid chlorinase;
ambO5 (gene name);
welO5 (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
12-epi-fischerindole U,2-oxoglutarate:oxygen oxidoreductase (13-halogenating)
Reaction(IUBMB)
(1) hapalindole U + 2-oxoglutarate + O2 + chloride = hapalindole G + succinate + CO2 + H2O [RN:R12165];
(2)12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride = 12-epi-fischerindole G + succinate + CO2 + H2O [RN:R12166]
Reaction(KEGG)
Substrate
hapalindole U [CPD:C21973];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007];
chloride [CPD:C00698];
12-epi-fischerindole U [CPD:C21840]
Product
hapalindole G [CPD:C21974];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001];
12-epi-fischerindole G [CPD:C21975]
Comment
The enzyme, characterized from hapalindole-type alkaloids-producing cyanobacteria, is a specialized iron(II)/2-oxoglutarate-dependent oxygenase that catalyses the chlorination of its substrates in a reaction that requires oxygen, chloride ions, iron(II) and 2-oxoglutarate.
History
EC 1.14.20.14 created 2018
Orthology
K22996  hapalindole-type alkaloid chlorinase
Reference
1  [PMID:25218740]
  Authors
Hillwig ML, Liu X
  Title
A new family of iron-dependent halogenases acts on freestanding substrates.
  Journal
Nat Chem Biol 10:921-3 (2014)
DOI:10.1038/nchembio.1625
Reference
2  [PMID:26749394]
  Authors
Zhu Q, Hillwig ML, Doi Y, Liu X
  Title
Aliphatic Halogenase Enables Late-Stage C-H Functionalization: Selective Synthesis of a Brominated Fischerindole Alkaloid with Enhanced Antibacterial Activity.
  Journal
Chembiochem 17:466-70 (2016)
DOI:10.1002/cbic.201500674
Reference
3  [PMID:27027281]
  Authors
Hillwig ML, Zhu Q, Ittiamornkul K, Liu X
  Title
Discovery of a Promiscuous Non-Heme Iron Halogenase in Ambiguine Alkaloid Biogenesis: Implication for an Evolvable Enzyme Family for Late-Stage Halogenation of Aliphatic Carbons in Small Molecules.
  Journal
Angew Chem Int Ed Engl 55:5780-4 (2016)
DOI:10.1002/anie.201601447
Other DBs
ExplorEnz - The Enzyme Database: 1.14.20.14
IUBMB Enzyme Nomenclature: 1.14.20.14
ExPASy - ENZYME nomenclature database: 1.14.20.14
BRENDA, the Enzyme Database: 1.14.20.14

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