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IUBMB 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.
Synonyms EasG ,
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agroclavine synthase
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EasG
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agroclavine + NADP+ = 6,8-dimethyl-6,7,8,9-tetradehydroergoline + NADPH + H+
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MetaCyc
ergotamine biosynthesis
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agroclavine:NADP+ oxidoreductase
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.
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(8beta,10beta)-6-amino-8-methyl-6,7-didehydroergolin-6-ium + NADPH + H+
festuclavine + NADP+
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Substrates: -
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6,8-dimethyl-6,7,8,9-tetradehydroergoline + NADPH + H+
agroclavine + NADP+
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Substrates: -
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chanoclavine-I aldehyde + GSH + NADPH + H+
agroclavine + GSSG + NADP+
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Substrates: the reaction occurs only in the presence of reduced glutathione
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chanoclavine-I aldehyde + NADH + H+
agroclavine + NAD+
chanoclavine-I aldehyde + NADPH + H+
agroclavine + NADP+
chanoclavine-I aldehyde + NADPH + H+
festuclavine + pyroclavine + NADP+
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Substrates: -
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chanoclavine-I aldehyde + NADH + H+
agroclavine + NAD+
Substrates: 54% conversion compared to NADPH, in the presence of reduced glutathione
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chanoclavine-I aldehyde + NADH + H+
agroclavine + NAD+
Substrates: the reaction occurs only in the presence of reduced glutathione (conversion rate of 54%)
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chanoclavine-I aldehyde + NADPH + H+
agroclavine + NADP+
Substrates: the reaction occurs only in the presence of reduced glutathione or beta-mercaptoethanol or dithiothreitol
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chanoclavine-I aldehyde + NADPH + H+
agroclavine + NADP+
Substrates: the reaction occurs only in the presence of the thiolation agents reduced glutathione (conversion rate of 59%) or 2-mercaptoethanol (conversion rate of 99%) and dithiothreitol (conversion rate of 67%). No product formation is detected in the incubation mixture with L-ascorbic acid instead of GSH
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NADPH
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NADPH
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NADPH is a better electron donor than NADH
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reduced glutathione
required for activity
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UniProt
brenda
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Highest Expressing Human Cell Lines
Filter by:
Cell Line Links
Gene Links
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EASG_CLAFS
289
0
31815
Swiss-Prot
other Location (Reliability: 3 )
EASG_CLAP2
Claviceps purpurea (strain 20.1)
290
0
31904
Swiss-Prot
Mitochondrion (Reliability: 2 )
EASG_CLAPU
290
0
31890
Swiss-Prot
Mitochondrion (Reliability: 2 )
EASG_EPIFI
309
0
34267
Swiss-Prot
other Location (Reliability: 4 )
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33300
1 * 33300, His-tagged enzyme, calculated from amino acid sequence
30000
1 * 30000, His-tagged enzyme, SDS-PAGE
30000
x * 30000, His-tagged enzyme, SDS-PAGE
31900
1 * 31900, native enzyme, calculated from amino acid sequence
31900
x * 31900, calculated from amino acid sequence
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x * 30000, His-tagged enzyme, SDS-PAGE
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x * 31900, calculated from amino acid sequence
monomer
1 * 30000, His-tagged enzyme, SDS-PAGE
monomer
1 * 31900, native enzyme, calculated from amino acid sequence
monomer
1 * 33300, His-tagged enzyme, calculated from amino acid sequence
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Ni-NTA agarose column chromatography
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expressed in Escherichia coli BXL1 Blue MRF cells
expressed in Escherichia coli strain XL1 Blue MRF
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Cheng, J.; Coyle, C.; Panaccione, D.; OConnor, S.
Controlling a structural branch point in ergot alkaloid biosynthesis
J. Am. Chem. Soc.
132
12835-12837
2010
Aspergillus fumigatus
brenda
Matuschek, M.; Wallwey, C.; Xie, X.; 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
4328-4335
2011
Claviceps purpurea, Claviceps purpurea (P0CT21)
brenda
Matuschek, M.; Wallwey, C.; Wollinsky, B.; Xie, X.; Li, S.
In vitro conversion of chanoclavine-I aldehyde to the stereoisomers festuclavine and pyroclavine controlled by the second reduction step
RSC Adv.
2
3662-3669
2012
Claviceps purpurea
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brenda
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