KEGG   ENZYME: 1.3.1.123
Entry
EC 1.3.1.123                Enzyme                                 
Name
8-oxogeranial reductase;
AmISY
Class
Oxidoreductases;
Acting on the CH-CH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
(R)-8-oxocitronellyl enol:NADP+ oxidoreductase
Reaction(IUBMB)
(R)-8-oxocitronellyl enol + NADP+ = (6E)-8-oxogeranial + NADPH + H+ [RN:R12519]
Reaction(KEGG)
R12519
Substrate
(R)-8-oxocitronellyl enol [CPD:C20615];
NADP+ [CPD:C00006]
Product
(6E)-8-oxogeranial [CPD:C17622];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
The enzyme, characterized from the plant Antirrhinum majus (snapdragon), is involved in biosynthesis of 7-epi-iridoids such as antirrhinoside. The enzyme catalyses the stereospecific reduction of 8-oxogeranial, forming an unstable product that in the absence of additional cylases undergoes spontaneous cyclization to (-)-cis,trans-nepetalactol. cf. EC 1.3.1.122, (S)-8-oxocitronellyl enol synthase.
History
EC 1.3.1.123 created 2019
Orthology
K23968  8-oxogeranial reductase
Genes
SIND: 105155584
APAN: 127256872
Reference
1  [PMID:28701463]
  Authors
Kries H, Kellner F, Kamileen MO, O'Connor SE
  Title
Inverted stereocontrol of iridoid synthase in snapdragon.
  Journal
J Biol Chem 292:14659-14667 (2017)
DOI:10.1074/jbc.M117.800979
  Sequence
[ag:ASM61954]
Reference
2  [PMID:30664302]
  Authors
Lichman BR, O'Connor SE, Kries H
  Title
Biocatalytic Strategies towards [4+2] Cycloadditions.
  Journal
Chemistry 25:6864-6877 (2019)
DOI:10.1002/chem.201805412
Other DBs
ExplorEnz - The Enzyme Database: 1.3.1.123
IUBMB Enzyme Nomenclature: 1.3.1.123
ExPASy - ENZYME nomenclature database: 1.3.1.123
BRENDA, the Enzyme Database: 1.3.1.123

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Chemical substance (5)   
   KEGG COMPOUND (5)   
Chemical reaction (1)   
   KEGG REACTION (1)   
Gene (4)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (3)   
Protein sequence (2)   
   UniProt (1)   
   SWISS-PROT (1)   
Protein domain (1)   
   InterPro (1)   
All databases (13)   

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