The Enzyme Database

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EC 5.5.1.31     
Accepted name: hapalindole H synthase
Reaction: 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = hapalindole H
For diagram of Hapalindole/Fischerindole biosynthesis, click here
Glossary: hapalindole H = (6aR,9R,10R,10aR)-9-ethenyl-1-isocyano-6,6,9-trimethyl-2,6,6a,7,8,9,10,10a-decahydronaphtho[1,2,3-cd]indole
Other name(s): famC2 (gene name); famC3 (gene name)
Systematic name: 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole cyclase (hapalindole H-forming)
Comments: The enzyme, characterized from the cyanobacterium Fischerella ambigua UTEX 1903, forms the core structure of the hapalindole family of alkaloids. The enzyme is a heterodimeric complex.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
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 5.5.1.31 created 2018]
 
 
EC 5.5.1.32     
Accepted name: 12-epi-hapalindole U synthase
Reaction: 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = 12-epi-hapalindole U
For diagram of Hapalindole/Fischerindole biosynthesis, click here
Glossary: 12-epi-hapalindole H = (6aR,9S,10R,10aR)-9-ethenyl-1-isocyano-6,6,9-trimethyl-2,6,6a,7,8,9,10,10a-decahydronaphtho[1,2,3-cd]indole
Other name(s): famC1 (gene name); HpiC1 (gene name)
Systematic name: 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole cyclase (12-epi-hapalindole U-forming)
Comments: The enzyme, characterized from the cyanobacterium Fischerella ambigua UTEX 1903, forms the core structure of the 12-epi-hapalindole family of alkaloids.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Li, S., Lowell, A.N., Yu, F., Raveh, A., Newmister, S.A., Bair, N., Schaub, J.M., Williams, R.M. and Sherman, D.H. Hapalindole/ambiguine biogenesis Is mediated by a Cope rearrangement, C-C bond-forming cascade. J. Am. Chem. Soc. 137 (2015) 15366–15369. [DOI] [PMID: 26629885]
[EC 5.5.1.32 created 2018]
 
 


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