Information on EC 4.2.3.48 - (3S,6E)-nerolidol synthase

New: Word Map on EC 4.2.3.48
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Magnoliophyta

EC NUMBER
COMMENTARY
4.2.3.48
-
RECOMMENDED NAME
GeneOntology No.
(3S,6E)-nerolidol synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate + H2O = (3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(3E)-4,8-dimethylnona-1,3,7-triene biosynthesis
-
-
Sesquiterpenoid and triterpenoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(3S,6E)-nerolidol-forming]
The enzyme catalyses a step in the formation of (3E)-4,8-dimethylnona-1,3,7-triene, a key signal molecule in induced plant defense mediated by the attraction of enemies of herbivores [2]. Nerolidol is a naturally occurring sesquiterpene found in the essential oils of many types of plants.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
(3S)-(E)-nerolidol synthase
-
-
FaNES1
-
gene name
linalool/nerolidol synthase
-
-
MtTPS3
Q5UB06
gene name
nerolidol/geranyl linalool synthase
Q5UB06
-
NES1
H9M5U5
-
NES1
P0CV94
-
TPS3
F8TWD1
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
wild-type cv. Jemalong
UniProt
Manually annotated by BRENDA team
cv. Sieva
-
-
Manually annotated by BRENDA team
sequence contains a plastid targeting signal peptide
UniProt
Manually annotated by BRENDA team
cv. Delprim
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
P0CV94
introduction of the mitochondrial nerolidol synthase gene to Arabidopsis thaliana mediates de novo emission of (E)-nerolidol and linalool. Co-expression of the nerolidol synthase FPS1 and cytosolic 3-hydroxy-3-methylglutaryl coenzyme A reductase 1 increases the number of emitting transgenic plants (incidence rate) and the emission rate of both volatiles. No association between the emission rate of transgenic volatiles and their growth inhibitory effect can be established.(E)-Nerolidol is to a large extent metabolized to non-volatile conjugates
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
F8TWD1
-
single product, almost exclusive product
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
-
almost exclusive product
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
H9M5U5
-
predominant enantiomer produced
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
(3S)-(E)-nerolidol synthase plays an important role in regulating the formation of 4,8-dimethyl-1,3(E),7-nonatriene, a key signal molecule in induced plant defense mediated by the attraction of enemies of herbivores
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
biosynthesis of the C11 homoterpene (3E)-4,8-dimethyl-1,3,7-nonatriene
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
Q5UB06
MtTPS3 produces linalool at 5% of the rate of (E)-nerolidol. Using geranylgeranyl diphosphate the enzyme fails to produce diterpenoids. The recombinant MtTPS3 generates the diterpene geranyllinalool when supplied with geranylgeranyl diphosphate (65% of the rate of (E)-nerolidol)
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
the enzyme also converts geranyl diphosphate to (3S)-linalool, EC 4.2.3.25 (S-linalool synthase)
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
the enzymer does not form linalool or other metabolites from geranyl diphosphate
-
-
?
geranyl diphosphate + H2O
(S)-linalool + diphosphate
show the reaction diagram
H9M5U5
58% of the velocity with (2E,6E)-farnesyl diphosphate
-
-
?
geranylgeranyl diphosphate + H2O
geranyl linalool + diphosphate
show the reaction diagram
H9M5U5
10% of the velocity with (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
H9M5U5
no substrate: dimethylallyl diphosphate
-
-
-
additional information
?
-
F8TWD1
Populus trichocarpa TPS3 additionally accepts geranyl diphosphate to produce (3S)-linalool. No substrate: geranylgeranyl diphosphate
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
(3S)-(E)-nerolidol synthase plays an important role in regulating the formation of 4,8-dimethyl-1,3(E),7-nonatriene, a key signal molecule in induced plant defense mediated by the attraction of enemies of herbivores
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
show the reaction diagram
-
biosynthesis of the C11 homoterpene (3E)-4,8-dimethyl-1,3,7-nonatriene
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Co2+
-
nerolidol synthase is completely inactive in the absence of added divalent metal ion. Mg2+ is most effective. Co2+ shows 11% of the activity compared to Mg2+
Cu2+
-
nerolidol synthase is completely inactive in the absence of added divalent metal ion. Mg2+ is most effective. Cu2+ shows 12% of the activity compared to Mg2+
Mg2+
-
nerolidol synthase is completely inactive in the absence of added divalent metal ion. Mg2+ is most effective. Other divalent cations are less effective in supporting catalysis. Metal ions in order of edcreasing efficiency: Mg2+, Mn2+, Co2+, Cu2+, Ni2+, Zn2+. KM-value for Mg2+ is 0.125 mM
Mg2+
H9M5U5
Km value 0.117 mM
Mn2+
-
nerolidol synthase is completely inactive in the absence of added divalent metal ion. Mn2+ is half as effective as Mg2+ at 1 mM, inhibits at higher concentrations
Mn2+
H9M5U5
Km value 0.014 mM
Ni2+
-
nerolidol synthase is completely inactive in the absence of added divalent metal ion. Mg2+ is most effective. Ni2+ shows 17% of the activity compared to Mg2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
EDTA
-
1 mM, activity is fully restored by the addition of Mg2+ to a saturating concentration of 1 mM. Mn2+ is about half as effective as Mg2+ at 1 mM
Mn2+
-
activates at 1 mM, inhibits at higher concentrations
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0008
(2E,6E)-farnesyl diphosphate
H9M5U5
pH 7.5, 22C, presence of Mg2+
0.0038
(2E,6E)-farnesyl diphosphate
-
-
0.0081
(2E,6E)-farnesyl diphosphate
-
-
0.0019
geranyl diphosphate
H9M5U5
pH 7.5, 22C, presence of Mg2+
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.24
(2E,6E)-farnesyl diphosphate
H9M5U5
pH 7.5, 22C, presence of Mg2+
0.03
geranyl diphosphate
H9M5U5
pH 7.5, 22C, presence of Mn2+
0.13
geranyl diphosphate
H9M5U5
pH 7.5, 22C, presence of Mg2+
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
300
(2E,6E)-farnesyl diphosphate
H9M5U5
pH 7.5, 22C, presence of Mg2+
81
69
geranyl diphosphate
H9M5U5
pH 7.5, 22C, presence of Mg2+
175
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.4 - 7.2
-
50% of maximal activity at pH 6.4 and pH 7.2
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
FaNES1 is strongly expressed in cultivated strawberry (octaploid) varieties but hardly expressed at all in wild strawberry species. Increase in FaNES1 transcript levels during fruit ripening
Manually annotated by BRENDA team
-
leaves fed upon by Spodoptera littoralis
Manually annotated by BRENDA team
-
slightly active in uninfested lima bean leaves, and strongly induced by feeding of the two-spotted spider mite (Tetranychus urticae Koch) on both plant species, but not by mechanical wounding
Manually annotated by BRENDA team
-
the enzyme is inactives in uninfested lima bean leaves, and strongly induced by feeding of the two-spotted spider mite (Tetranychus urticae Koch) on both plant species, but not by mechanical wounding
Manually annotated by BRENDA team
-
volatile compounds induced by Lymantria dispar feeding
Manually annotated by BRENDA team
additional information
-
no expression detected in leaf tissue
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
50000
-
gel filtration
706369
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
H9M5U5
x * 65400, calculated
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, stable for 1 week
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Lactococcus lactis and actively expressed using the nisin-induced expression system
-
recombinant FaNES1 enzyme produced in Escherichia coli cells is capable of generating both linalool and nerolidol when supplied with geranyl diphosphate or farnesyl diphosphate, respectively
-
subcloned into the pHis83 expression vector and transformed into Escherichia coli BL21-CodonPlus(DE3)
Q5UB06
expression in Escherichia coli; expression in Escherichia coli
F8TWD1
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
peak expression of enzyme correlates with peak (E)-nerolidol, but not linalool accumulation in flowers
H9M5U5
the enzyme is inactive in uninfested cucumber leaves, and strongly induced by feeding of the two-spotted spider mite (Tetranychus urticae Koch) on both plant species, but not by mechanical wounding
-
increase in FaNES1 transcript levels during fruit ripening
-
MtTPS3 activity is induced by jasmonic acid ((E)-4,8-dimethyl-1,3,7-nonatriene) and by jasmonic acid + (E)-nerolidol. Feeding Beet armyworm raises the expression level of MtTPS3 in wild-type and skl plants in the same way, but levels of (E)-nerolidol and (E)-4,8-dimethyl-1,3,7-nonatriene formation are higher in wild-type plants, suggesting that ethylene might have a post-transcriptional impact on the MtTPS3 protein
Q5UB06
slightly active in uninfested lima bean leaves, and strongly induced by feeding of the two-spotted spider mite (Tetranychus urticae Koch) on both plant species, but not by mechanical wounding
-
induced by Lymantria dispar feeding
F8TWD1
induced by Lymantria dispar feeding, up to 136fold increase in transcript abundance
F8TWD1
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
P0CV94
introduction of the mitochondrial nerolidol synthase gene to Arabidopsis thaliana mediates de novo emission of (E)-nerolidol and linalool. Co-expression of the nerolidol synthase FPS1 and cytosolic 3-hydroxy-3-methylglutaryl coenzyme A reductase 1 increases the number of emitting transgenic plants (incidence rate) and the emission rate of both volatiles. No association between the emission rate of transgenic volatiles and their growth inhibitory effect can be established.(E)-Nerolidol is to a large extent metabolized to non-volatile conjugates