The Enzyme Database

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EC 1.3.1.100     
Accepted name: chanoclavine-I aldehyde reductase
Reaction: dihydrochanoclavine-I aldehyde + NADP+ = chanoclavine-I aldehyde + NADPH + H+
For diagram of fumigaclavin alkaloid biosynthesis, click here
Glossary: chanoclavine-I aldehyde = (1E)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenz[cd]indol-5-yl]prop-2-enal
Other name(s): FgaOx3; easA (gene name)
Systematic name: chanoclavine-I aldehyde:NAD+ oxidoreductase
Comments: Contains FMN. The enzyme participates in the biosynthesis of fumigaclavine C, an ergot alkaloid produced by some fungi of the Trichocomaceae family. The enzyme catalyses the reduction of chanoclavine-I aldehyde to dihydrochanoclavine-I aldehyde. This hydrolyses spontaneously to form 6,8-dimethyl-6,7-didehydroergoline, which is converted to festuclavine by EC 1.5.1.44, festuclavine dehydrogenase.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Coyle, C.M., Cheng, J.Z., O'Connor, S.E. and Panaccione, D.G. An old yellow enzyme gene controls the branch point between Aspergillus fumigatus and Claviceps purpurea ergot alkaloid pathways. Appl. Environ. Microbiol. 76 (2010) 3898–3903. [DOI] [PMID: 20435769]
2.  Cheng, J.Z., Coyle, C.M., Panaccione, D.G. and O'Connor, S.E. A role for Old Yellow Enzyme in ergot alkaloid biosynthesis. J. Am. Chem. Soc. 132 (2010) 1776–1777. [DOI] [PMID: 20102147]
3.  Wallwey, C., Matuschek, M., Xie, X.L. and Li, S.M. Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3. Org. Biomol. Chem. 8 (2010) 3500–3508. [DOI] [PMID: 20526482]
4.  Xie, X., Wallwey, C., Matuschek, M., Steinbach, K. and Li, S.M. Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: a NMR structure elucidation. Magn. Reson. Chem. 49 (2011) 678–681. [DOI] [PMID: 21898587]
[EC 1.3.1.100 created 2013]
 
 
EC 1.5.1.44     
Accepted name: festuclavine dehydrogenase
Reaction: festuclavine + NAD+ = 6,8-dimethyl-6,7-didehydroergoline + NADH + H+
For diagram of fumigaclavin alkaloid biosynthesis, click here
Glossary: festuclavine = 6,8β-dimethylergoline
Other name(s): FgaFS; festuclavine synthase
Systematic name: festuclavine:NAD+ oxidoreductase
Comments: The enzyme participates in the biosynthesis of fumigaclavine C, an ergot alkaloid produced by some fungi of the Trichocomaceae family. The reaction proceeds in vivo in the opposite direction to the one shown here.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Wallwey, C., Matuschek, M., Xie, X.L. and Li, S.M. Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3. Org. Biomol. Chem. 8 (2010) 3500–3508. [DOI] [PMID: 20526482]
[EC 1.5.1.44 created 2012]
 
 
EC 2.3.1.205     
Accepted name: fumigaclavine B O-acetyltransferase
Reaction: acetyl-CoA + fumigaclavine B = CoA + fumigaclavine A
For diagram of fumigaclavin alkaloid biosynthesis, click here
Glossary: fumigaclavine B = 6,8β-dimethylergolin-9-ol;
fumigaclavine A = 6,8β-dimethylergolin-9β-yl acetate
Other name(s): FgaAT
Systematic name: acetyl-CoA:fumigaclavine B O-acetyltransferase
Comments: The enzyme participates in the biosynthesis of fumigaclavine C, an ergot alkaloid produced by some fungi of the Trichocomaceae family.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Liu, X., Wang, L., Steffan, N., Yin, W.B. and Li, S.M. Ergot alkaloid biosynthesis in Aspergillus fumigatus: FgaAT catalyses the acetylation of fumigaclavine B. ChemBioChem 10 (2009) 2325–2328. [DOI] [PMID: 19672909]
[EC 2.3.1.205 created 2012]
 
 
EC 2.5.1.100     
Accepted name: fumigaclavine A dimethylallyltransferase
Reaction: fumigaclavine A + dimethylallyl diphosphate = fumigaclavine C + diphosphate
For diagram of fumigaclavin alkaloid biosynthesis, click here
Glossary: fumigaclavine A = 6,8β-dimethylergolin-9β-yl acetate;
fumigaclavine C = 2-(2-methylbut-3-en-2-yl)-6,8β-dimethylergolin-9β-yl acetate
Other name(s): FgaPT1
Systematic name: dimethylallyl-diphosphate:fumigaclavine A dimethylallyltransferase
Comments: Fumigaclavine C is an ergot alkaloid produced by some fungi of the Trichocomaceae family. Activity does not require any metal ions.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Unsöld, I.A. and Li, S.M. Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: gene expression, purification, and characterization of fumigaclavine C synthase FGAPT1. ChemBioChem 7 (2006) 158–164. [DOI] [PMID: 16397874]
[EC 2.5.1.100 created 2012]
 
 


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