KEGG   ENZYME: 1.1.1.318Help
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
BRITE hierarchy
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
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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
Phenylpropanoid biosynthesis
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 (2006) 10128-33.
  Sequence
[up:Q15GI4]
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 (2007) 209-18.
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 (2007) e993.
  Sequence
[up:Q15GI4]
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 (2008) 362-74.
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 (2009) 384-94.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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