KEGG   ORTHOLOGY: K17055
Entry
K17055            Tight     KO                                     
Symbol
EGS1
Name
eugenol synthase [EC:1.1.1.318]
Pathway
map00940  Phenylpropanoid biosynthesis
map01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00940 Phenylpropanoid biosynthesis
    K17055  EGS1; eugenol 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
    1.1.1.318  eugenol synthase
     K17055  EGS1; eugenol synthase
Other DBs
RN: R10248 R10249
Genes
AG: ABD17321(EGS1)
Reference
  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
Reference
  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: 1.1.1.318
Entry
EC 1.1.1.318                Enzyme                                 
Name
eugenol synthase;
LtCES1;
EGS1;
EGS2
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
eugenol:NADP+ oxidoreductase (coniferyl ester reducing)
Reaction(IUBMB)
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH + H+ [RN:R09930]
Reaction(KEGG)
R09930 > R10248;
(other) R10249
Substrate
eugenol [CPD:C10453];
carboxylate [CPD:C00060];
NADP+ [CPD:C00006]
Product
coniferyl ester [CPD:C20224];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
The enzyme acts in the opposite direction. The enzymes from the plants Ocimum basilicum (sweet basil) [1,3], Clarkia breweri and Petunia hybrida [4] only accept coniferyl acetate and form eugenol. The enzyme from Pimpinella anisum (anise) forms anol (from 4-coumaryl acetate) in vivo, although the recombinant enzyme can form eugenol from coniferyl acetate [5]. The enzyme from Larrea tridentata (creosote bush) also forms chavicol from a coumaryl ester and can use NADH [2].
History
EC 1.1.1.318 created 2012
Pathway
ec00940  Phenylpropanoid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K17055  eugenol 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
Reference
2  [PMID:17624297]
  Authors
Vassao DG, Kim SJ, Milhollan JK, Eichinger D, Davin LB, Lewis NG
  Title
A pinoresinol-lariciresinol reductase homologue from the creosote bush (Larrea tridentata) catalyzes the efficient in vitro conversion of p-coumaryl/coniferyl alcohol esters into the allylphenols chavicol/eugenol, but not the propenylphenols p-anol/isoeugenol.
  Journal
Arch Biochem Biophys 465:209-18 (2007)
DOI:10.1016/j.abb.2007.06.002
Reference
3  [PMID:17912370]
  Authors
Louie GV, Baiga TJ, Bowman ME, Koeduka T, Taylor JH, Spassova SM, Pichersky E, Noel JP
  Title
Structure and reaction mechanism of basil eugenol synthase.
  Journal
PLoS One 2:e993 (2007)
DOI:10.1371/journal.pone.0000993
  Sequence
Reference
4  [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
5  [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: 1.1.1.318
IUBMB Enzyme Nomenclature: 1.1.1.318
ExPASy - ENZYME nomenclature database: 1.1.1.318
BRENDA, the Enzyme Database: 1.1.1.318
LinkDB

KEGG   REACTION: R10248
Entry
R10248                      Reaction                               
Name
eugenol:NADP+ oxidoreductase (coniferyl ester reducing)
Definition
Coniferyl acetate + NADPH + H+ <=> Eugenol + NADP+ + Acetate
Equation
Reaction class
RC00001  C00005_C00006
RC00020  C00033_C20225
RC02844  C10453_C20225
Enzyme
Pathway
rn00940  Phenylpropanoid biosynthesis
Orthology
K17055  eugenol synthase [EC:1.1.1.318]
Other DBs
RHEA: 24693
LinkDB

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