EC |
1.3.1.100 |
Accepted name: |
chanoclavine-I aldehyde reductase |
Reaction: |
dihydrochanoclavine-I aldehyde + NADP+ = chanoclavine-I aldehyde + NADPH + H+ |
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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, PDB |
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] |
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[EC 1.3.1.100 created 2013] |
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EC |
1.5.1.44 |
Accepted name: |
festuclavine dehydrogenase |
Reaction: |
festuclavine + NAD+ = 6,8-dimethyl-6,7-didehydroergoline + NADH + H+ |
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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] |
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[EC 1.5.1.44 created 2012] |
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EC |
2.3.1.205 |
Accepted name: |
fumigaclavine B O-acetyltransferase |
Reaction: |
acetyl-CoA + fumigaclavine B = CoA + fumigaclavine A |
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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] |
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[EC 2.3.1.205 created 2012] |
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EC |
2.5.1.100 |
Accepted name: |
fumigaclavine A dimethylallyltransferase |
Reaction: |
fumigaclavine A + prenyl diphosphate = fumigaclavine C + diphosphate |
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For diagram of fumigaclavin alkaloid biosynthesis, click here |
Glossary: |
fumigaclavine A = 6,8β-dimethylergolin-9β-yl acetate;
fumigaclavine C = 6,8β-dimethyl-2-(2-methylbut-3-en-2-yl)ergolin-9β-yl acetate |
Other name(s): |
FgaPT1; dimethylallyl-diphosphate:fumigaclavine A dimethylallyltransferase |
Systematic name: |
prenyl-diphosphate:fumigaclavine A prenyltransferase |
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] |
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[EC 2.5.1.100 created 2012] |
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