KEGG   ORTHOLOGY: K19182
Entry
K19182                      KO                                     
Symbol
FGAOX3
Name
chanoclavine-I aldehyde reductase [EC:1.3.1.100]
Pathway
map00901  Indole alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00964  Fumigaclavine biosynthesis, chanoclavine-I aldehyde => fumigaclavine C
Reaction
R12090  chanoclavine-I aldehyde:NAD+ oxidoreductase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00901 Indole alkaloid biosynthesis
    K19182  FGAOX3; chanoclavine-I aldehyde reductase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.3  Acting on the CH-CH group of donors
   1.3.1  With NAD+ or NADP+ as acceptor
    1.3.1.100  chanoclavine-I aldehyde reductase
     K19182  FGAOX3; chanoclavine-I aldehyde reductase
Genes
MAW: 19251292(J3458_016185)
MAJ: MAA_06743
MBRN: 26246257(G6M90_00g054530)
GLZ: GLAREA_05926
AFM: AFUA_2G17960
Reference
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
[afm:AFUA_2G17960]
LinkDB

KEGG   ENZYME: 1.3.1.100
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
Sysname
chanoclavine-I aldehyde:NAD+ oxidoreductase
Reaction(IUBMB)
dihydrochanoclavine-I aldehyde + NADP+ = chanoclavine-I aldehyde + NADPH + H+ [RN:R12090]
Reaction(KEGG)
R12090
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
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K19182  chanoclavine-I aldehyde reductase
Genes
MAW: 19251292(J3458_016185)
MAJ: MAA_06743
MBRN: 26246257(G6M90_00g054530)
GLZ: GLAREA_05926
AFM: AFUA_2G17960
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
[afm:AFUA_2G17960]
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
[afm:AFUA_2G17960]
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
[afm:AFUA_2G17960]
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
LinkDB

KEGG   REACTION: R12090
Entry
R12090                      Reaction                               
Name
chanoclavine-I aldehyde:NAD+ oxidoreductase
Definition
Dihydrochanoclavine-I aldehyde + NADP+ <=> Chanoclavine-I aldehyde + NADPH + H+
Equation
C21897 + C00006 <=> C20379 + C00005 + C00080
Reaction class
RC03527  C20379_C21897
Enzyme
1.3.1.100
Pathway
rn00901  Indole alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00964  Fumigaclavine biosynthesis, chanoclavine-I aldehyde => fumigaclavine C
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.3  Acting on the CH-CH group of donors
   1.3.1  With NAD+ or NADP+ as acceptor
    1.3.1.100
     R12090  Dihydrochanoclavine-I aldehyde + NADP+ <=> Chanoclavine-I aldehyde + NADPH + H+
Orthology
K19182  chanoclavine-I aldehyde reductase [EC:1.3.1.100]
Reference
1  [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
LinkDB

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