KEGG ENZYME: 1.14.20.14

ENZYME: 1.14.20.14

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

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)

R12165 R12166

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

All links

Chemical substance (10)   
   KEGG COMPOUND (10)   
Chemical reaction (3)   
   KEGG REACTION (2)   
   KEGG RCLASS (1)   
Gene (3)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (2)   
All databases (16)   

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