EC |
1.1.1.332 |
Accepted name: |
chanoclavine-I dehydrogenase |
Reaction: |
chanoclavine-I + NAD+ = chanoclavine-I aldehyde + NADH + H+ |
Glossary: |
chanoclavine-I = (1E)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenz[cd]indol-5-yl]prop-2-en-1-ol
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): |
easD (gene name); fgaDH (gene name) |
Systematic name: |
chanoclavine-I:NAD+ oxidoreductase |
Comments: |
The enzyme catalyses a step in the pathway of ergot alkaloid biosynthesis in certain fungi. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Wallwey, C., Matuschek, M. and Li, S.M. Ergot alkaloid biosynthesis in Aspergillus fumigatus: conversion of chanoclavine-I to chanoclavine-I aldehyde catalyzed by a short-chain alcohol dehydrogenase FgaDH. Arch. Microbiol. 192 (2010) 127–134. [DOI] [PMID: 20039019] |
2. |
Wallwey, C., Heddergott, C., Xie, X., Brakhage, A.A. and Li, S.M. Genome mining reveals the presence of a conserved gene cluster for the biosynthesis of ergot alkaloid precursors in the fungal family Arthrodermataceae. Microbiology 158 (2012) 1634–1644. [DOI] [PMID: 22403186] |
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[EC 1.1.1.332 created 2012] |
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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+ |
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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 |
1.5.1.46 |
Accepted name: |
agroclavine dehydrogenase |
Reaction: |
agroclavine + NADP+ = 6,8-dimethyl-6,7,8,9-tetradehydroergoline + NADPH + H+ |
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For diagram of ergot alkaloid biosynthesis, click here |
Glossary: |
agroclavine = 6,8-dimethyl-8,9-didehydroergoline |
Other name(s): |
easG (gene name) |
Systematic name: |
agroclavine:NADP+ oxidoreductase |
Comments: |
The enzyme participates in the biosynthesis of ergotamine, an ergot alkaloid produced by some fungi of the Clavicipitaceae family. The reaction is catalysed in the opposite direction to that shown. The substrate for the enzyme is an iminium intermediate that is formed spontaneously from chanoclavine-I aldehyde in the presence of glutathione. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Matuschek, M., Wallwey, C., Xie, X. and Li, S.M. New insights into ergot alkaloid biosynthesis in Claviceps purpurea: an agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine. Org. Biomol. Chem. 9 (2011) 4328–4335. [DOI] [PMID: 21494745] |
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[EC 1.5.1.46 created 2013] |
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