The Enzyme Database

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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, festuclavine dehydrogenase.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
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. [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. [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. [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. [PMID: 21898587]
[EC created 2013]

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