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+ [RN:R12090]
Reaction(KEGG)
Substrate
dihydrochanoclavine-I aldehyde [CPD:C21897];
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
Pathway
ec00901  Indole alkaloid biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K19182  chanoclavine-I aldehyde reductase
Genes
MAW: MAC_06981
MAJ: MAA_06743
GLZ: GLAREA_05926
AFM: AFUA_2G17960
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 76:3898-903 (2010)
DOI:10.1128/AEM.02914-09
  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 132:1776-7 (2010)
DOI:10.1021/ja910193p
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 8:3500-8 (2010)
DOI:10.1039/c003823g
  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 49:678-81 (2011)
DOI:10.1002/mrc.2796
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.3.1.100
IUBMB Enzyme Nomenclature: 1.3.1.100
ExPASy - ENZYME nomenclature database: 1.3.1.100
BRENDA, the Enzyme Database: 1.3.1.100

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