ExplorEnz: EC 1.14.20.14

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1.14.20.14

Accepted name:

hapalindole-type alkaloid chlorinase

Reaction:

(1) hapalindole U + 2-oxoglutarate + O₂ + chloride = hapalindole G + succinate + CO₂ + H₂O
(2)12-epi-fischerindole U + 2-oxoglutarate + O₂ + chloride = 12-epi-fischerindole G + succinate + CO₂ + H₂O

For diagram of hapalindole/fischerindole biosynthesis, click here

Glossary:

12-epi-fischerindole U = (6aS,9S,10R,10aS)-9-ethenyl-10-isocyano-6,6,9-trimethyl-5,6,6a,7,8,9,10,10a-octahydroindeno[2,1-b]indole
12-epi-fischerindole G = (6aR,8R,9S,10R,10aS)-8-chloro-9-ethenyl-10-isocyano-6,6,9-trimethyl-5,6,6a,7,8,9,10,10a-octahydroindeno[2,1-b]indole

Other name(s):

ambO5 (gene name); welO5 (gene name)

Systematic name:

12-epi-fischerindole U,2-oxoglutarate:oxygen oxidoreductase (13-halogenating)

Comments:

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.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Hillwig, M.L. and Liu, X. A new family of iron-dependent halogenases acts on freestanding substrates. Nat. Chem. Biol. 10 (2014) 921–923. [PMID: 25218740]
2.	Zhu, Q., Hillwig, M.L., Doi, Y. and Liu, X. Aliphatic halogenase enables late-stage C-H functionalization: selective synthesis of a brominated fischerindole alkaloid with enhanced antibacterial activity. ChemBioChem 17 (2016) 466–470. [PMID: 26749394]
3.	Hillwig, M.L., Zhu, Q., Ittiamornkul, K. and Liu, X. 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. Angew. Chem. Int. Ed. Engl. 55 (2016) 5780–5784. [PMID: 27027281]

[EC 1.14.20.14 created 2018]