KEGG   ORTHOLOGY: K17056
Entry
K17056            Tight     KO                                     
Symbol
IGS1
Name
isoeugenol synthase [EC:1.1.1.319]
Pathway
map00940  Phenylpropanoid biosynthesis
map01110  Biosynthesis of secondary metabolites
Reaction
R09931  eugenol:NADP+ oxidoreductase (coniferyl acetate reducing)
R10289  isochavicol:NADP+ oxidoreductase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00940 Phenylpropanoid biosynthesis
    K17056  IGS1; isoeugenol synthase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.319  isoeugenol synthase
     K17056  IGS1; isoeugenol synthase
Genes
AG: ABD17322(IGS1)
Reference
PMID:16782809
  Authors
Koeduka T, Fridman E, Gang DR, Vassao DG, Jackson BL, Kish CM, Orlova I, Spassova SM, Lewis NG, Noel JP, Baiga TJ, Dudareva N, Pichersky E
  Title
Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester.
  Journal
Proc Natl Acad Sci U S A 103:10128-33 (2006)
DOI:10.1073/pnas.0603732103
  Sequence
[ag:ABD17322]
Reference
PMID:18987218
  Authors
Koeduka T, Baiga TJ, Noel JP, Pichersky E
  Title
Biosynthesis of t-anethole in anise: characterization of t-anol/isoeugenol synthase and an O-methyltransferase specific for a C7-C8 propenyl side chain.
  Journal
Plant Physiol 149:384-94 (2009)
DOI:10.1104/pp.108.128066
LinkDB

KEGG   ENZYME: 1.1.1.319
Entry
EC 1.1.1.319                Enzyme                                 
Name
isoeugenol synthase;
IGS1;
t-anol/isoeugenol synthase 1
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
eugenol:NADP+ oxidoreductase (coniferyl acetate reducing)
Reaction(IUBMB)
isoeugenol + acetate + NADP+ = coniferyl acetate + NADPH + H+ [RN:R09931]
Reaction(KEGG)
R09931;
(other) R10289
Substrate
isoeugenol [CPD:C10469];
acetate [CPD:C00033];
NADP+ [CPD:C00006]
Product
coniferyl acetate [CPD:C20225];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
The enzyme acts in the opposite direction. In Ocimum basilicum (sweet basil), Clarkia breweri and Petunia hybrida only isoeugenol is formed [1,2]. However in Pimpinella anisum (anise) only anol is formed in vivo, although the cloned enzyme does produce isoeugenol [3].
History
EC 1.1.1.319 created 2012
Pathway
ec00940  Phenylpropanoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K17056  isoeugenol synthase
Reference
1  [PMID:16782809]
  Authors
Koeduka T, Fridman E, Gang DR, Vassao DG, Jackson BL, Kish CM, Orlova I, Spassova SM, Lewis NG, Noel JP, Baiga TJ, Dudareva N, Pichersky E
  Title
Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester.
  Journal
Proc Natl Acad Sci U S A 103:10128-33 (2006)
DOI:10.1073/pnas.0603732103
  Sequence
[ag:ABD17322]
Reference
2  [PMID:18208524]
  Authors
Koeduka T, Louie GV, Orlova I, Kish CM, Ibdah M, Wilkerson CG, Bowman ME, Baiga TJ, Noel JP, Dudareva N, Pichersky E
  Title
The multiple phenylpropene synthases in both Clarkia breweri and Petunia hybrida  represent two distinct protein lineages.
  Journal
Plant J 54:362-74 (2008)
DOI:10.1111/j.1365-313X.2008.03412.x
Reference
3  [PMID:18987218]
  Authors
Koeduka T, Baiga TJ, Noel JP, Pichersky E
  Title
Biosynthesis of t-anethole in anise: characterization of t-anol/isoeugenol synthase and an O-methyltransferase specific for a C7-C8 propenyl side chain.
  Journal
Plant Physiol 149:384-94 (2009)
DOI:10.1104/pp.108.128066
Other DBs
ExplorEnz - The Enzyme Database: 1.1.1.319
IUBMB Enzyme Nomenclature: 1.1.1.319
ExPASy - ENZYME nomenclature database: 1.1.1.319
BRENDA, the Enzyme Database: 1.1.1.319
LinkDB

KEGG   REACTION: R09931
Entry
R09931                      Reaction                               
Name
eugenol:NADP+ oxidoreductase (coniferyl acetate reducing)
Definition
Isoeugenol + Acetate + NADP+ <=> Coniferyl acetate + NADPH + H+
Equation
C10469 + C00033 + C00006 <=> C20225 + C00005 + C00080
Comment
multi-step reaction
intermediate (quinone methide [CPD:C20269])
Reaction class
RC00001  C00005_C00006
RC00020  C00033_C20225
RC02845  C10469_C20225
Enzyme
1.1.1.319
Pathway
rn00940  Phenylpropanoid biosynthesis
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.319
     R09931  Isoeugenol + Acetate + NADP+ <=> Coniferyl acetate + NADPH + H+
Orthology
K17056  isoeugenol synthase [EC:1.1.1.319]
Other DBs
RHEA: 24697
LinkDB

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