The Enzyme Database

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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
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 created 2018]
Accepted name: 12-epi-fischerindole U synthase
Reaction: 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = 12-epi-fischerindole U
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-5H,6aH,7H,8H,10H,10aH-indeno[2,1-b]indole
Other name(s): fisC (gene name); fimC5 (gene name)
Systematic name: 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole cyclase (12-epi-fischerindole U-forming)
Comments: The enzyme, characterized from multiple species of the cyanobacterial genus Fischerella, participates in the biosynthesis of the terpenoid indole alkaloids 12-epi-fischerindoles.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
1.  Li, S., Lowell, A.N., Newmister, S.A., Yu, F., Williams, R.M. and Sherman, D.H. Decoding cyclase-dependent assembly of hapalindole and fischerindole alkaloids. Nat. Chem. Biol. 13 (2017) 467–469. [DOI] [PMID: 28288107]
[EC created 2018]

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