KEGG   ENZYME: 1.3.1.100Help
Entry
EC 1.3.1.100                Enzyme                                 

Name
chanoclavine-I aldehyde reductase;
FgaOx3;
easA (gene name)
Class
Oxidoreductases;
Acting on the CH-CH group of donors;
With NAD+ or NADP+ as acceptor
BRITE hierarchy
Sysname
chanoclavine-I aldehyde:NAD+ oxidoreductase
Reaction(IUBMB)
dihydrochanoclavine-I aldehyde + NADP+ = chanoclavine-I aldehyde + NADPH + H+
Substrate
dihydrochanoclavine-I aldehyde;
NADP+ [CPD:C00006]
Product
chanoclavine-I aldehyde [CPD:C20379];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
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.
History
EC 1.3.1.100 created 2013
Orthology
K19182  
chanoclavine-I aldehyde reductase
Genes
MAW: 
MAJ: 
AFM: 
Taxonomy
Reference
1  [PMID:20435769]
  Authors
Coyle CM, Cheng JZ, O'Connor SE, Panaccione DG
  Title
An old yellow enzyme gene controls the branch point between Aspergillus fumigatus and Claviceps purpurea ergot alkaloid pathways.
  Journal
Appl. Environ. Microbiol. 76 (2010) 3898-903.
  Sequence
Reference
2  [PMID:20102147]
  Authors
Cheng JZ, Coyle CM, Panaccione DG, O'Connor SE
  Title
A role for Old Yellow Enzyme in ergot alkaloid biosynthesis.
  Journal
J. Am. Chem. Soc. 132 (2010) 1776-7.
Reference
3  [PMID:20526482]
  Authors
Wallwey C, Matuschek M, Xie XL, Li SM
  Title
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.
  Journal
Org. Biomol. Chem. 8 (2010) 3500-8.
  Sequence
Reference
4  [PMID:21898587]
  Authors
Xie X, Wallwey C, Matuschek M, Steinbach K, Li SM
  Title
Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: a NMR structure elucidation.
  Journal
Magn. Reson. Chem. 49 (2011) 678-81.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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