Information on EC 4.2.3.25 - S-linalool synthase

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The expected taxonomic range for this enzyme is: Spermatophyta

EC NUMBER
COMMENTARY
4.2.3.25
-
RECOMMENDED NAME
GeneOntology No.
S-linalool synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
geranyl diphosphate + H2O = (3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
geranyl diphosphate + H2O = (3S)-linalool + diphosphate
show the reaction diagram
reaction mechanism
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
hydrolysis of phosphate bond
-
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
linalool biosynthesis II
-
Monoterpenoid biosynthesis
-
superpathway of linalool biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [(3S)-linalool-forming]
Requires Mn2+ or Mg2+ for activity. Neither (S)- nor (R)-linalyl diphosphate can act as substrate for the enzyme from the flower Clarkia breweri [1]. Unlike many other monoterpene synthases, only a single product, (3S)-linalool, is formed.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
(-)-linalool synthase
-
-
(S)-linalool synthase
D4N3A0
-
(S)-linalool synthase
D4N3A1
-
linalool synthase
-
-
linalool synthase
Q96376
-
linalool synthase
Fragaria sp.
-
-
linalool synthase
-
-
linalool synthase
C0KWV5, C0KWV7
-
linalool synthase
C0KWV3
-
linalool/nerolidol synthase
-
-
LIS
Fragaria sp.
-
-
S-linalool synthase
Q96376
-
S-linalool synthase
-
-
S-linalool synthase
-
-
additional information
-
the enzyme belongs to the family of isoprenoid synthases
CAS REGISTRY NUMBER
COMMENTARY
160477-81-6
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
Cereus peruvianus
-
-
-
Manually annotated by BRENDA team
Fragaria sp.
-
-
-
Manually annotated by BRENDA team
no activity in Petunia hybrida
-
-
-
Manually annotated by BRENDA team
cv. Muscat de Frontignan
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-linalyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
low activity, 15% of the maximal activity with geranyl diphosphate
-
-
?
farnesyl diphosphate
nerolidol + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
Q96376
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
C0KWV5, C0KWV7, -
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
C0KWV3, -
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
D4N3A0
-
-
-
-
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
D4N3A1
-
-
-
-
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
Cereus peruvianus
-
enantio-specific reaction, the enzyme plays a pivotal role in production of flavor and aroma of ripe cactus fruits
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
enantio-specific reaction, the enzyme plays a pivotal role in production of flavor of ripe grape berries, production of free and bound S-linalool
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
recombinant enzyme in transgenic Petunia hybrida plants
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
wild-type enzyme in Clarkia breweri and recombinant enzyme in transgenic Lycopersicon esculentum plants, the enzyme is involved in the terpenoid pathway, overview, enantio-specific reaction
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
enantio-specific reaction
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
Cereus peruvianus
-
enantio-specific reaction, 85% optical puritiy of S-linalool
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
enantiospecific reaction
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
recombinant enzyme from transgenic Petunia hybrida plants
product identification
-
?
geranyl diphosphate + H2O
3,7-dimethyl-1,6-octadien-3-ol + diphosphate
show the reaction diagram
Fragaria sp.
-
-
linalool is a C10 monoterpene volatile present in the floral fragrance of diverse plant families
-
?
geranyl diphosphate + H2O
S-linalool + diphosphate
show the reaction diagram
-
isoprenoid pathway
-
-
?
additional information
?
-
-
Clarkia concinna is a non-scented species but does express linalool synthase at a low level
-
-
-
additional information
?
-
-
no activity with (R)-linalyl diphosphate
-
-
-
additional information
?
-
Cereus peruvianus
-
spontaneous enzyme-independent formation of racemic linalool from geranyl diphosphate in presence of Fe2+
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
Q96376
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
Cereus peruvianus
-
enantio-specific reaction, the enzyme plays a pivotal role in production of flavor and aroma of ripe cactus fruits
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
enantio-specific reaction, the enzyme plays a pivotal role in production of flavor of ripe grape berries, production of free and bound S-linalool
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
recombinant enzyme in transgenic Petunia hybrida plants
product identification
-
?
geranyl diphosphate + H2O
(3S)-linalool + diphosphate
show the reaction diagram
-
wild-type enzyme in Clarkia breweri and recombinant enzyme in transgenic Lycopersicon esculentum plants, the enzyme is involved in the terpenoid pathway, overview
-
-
?
geranyl diphosphate + H2O
3,7-dimethyl-1,6-octadien-3-ol + diphosphate
show the reaction diagram
Fragaria sp.
-
-
linalool is a C10 monoterpene volatile present in the floral fragrance of diverse plant families
-
?
geranyl diphosphate + H2O
S-linalool + diphosphate
show the reaction diagram
-
isoprenoid pathway
-
-
?
additional information
?
-
-
Clarkia concinna is a non-scented species but does express linalool synthase at a low level
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
-
half as effective as Mn2+
Mg2+
Cereus peruvianus
-
-
Mg2+
D4N3A0
Mg2+ or Mn2+ required
Mg2+
D4N3A1
Mg2+ or Mn2+ required
Mg2+
C0KWV5, C0KWV7, -
;
Mg2+
C0KWV3, -
-
Mn2+
-
absolutely required for activity, preferred divalent cation
Mn2+
Cereus peruvianus
-
preferred cation
Mn2+
D4N3A0
Mg2+ or Mn2+ required
Mn2+
D4N3A1
Mg2+ or Mn2+ required
Mn2+
C0KWV5, C0KWV7, -
;
Mn2+
C0KWV3, -
-
additional information
-
no activity with Cu2+, Zn2+, Ca2+, Co2+
additional information
Cereus peruvianus
-
divalent cation is required for activity, no activity with Cu2+, Co2+, and Ca2+, in presence of Fe2+ spontaneous enzyme-independent formation of racemic linalool from geranyl diphosphate occurs
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
SDS
-
leads to complete loss of activity at about 0.1%
additional information
-
no effects by 0.1% w/v Triton X-100
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
DTT
-
required for stability
DTT
Cereus peruvianus
-
-
insect herbivory
Fragaria sp.
-
-
-
methyl jasmonate
Fragaria sp.
-
induction of expression under the control of a wound-inducible promoter in Arapidopsis thaliana
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0009
-
geranyl diphosphate
-
pH 7.4, 20C
0.0021
-
geranyl diphosphate
D4N3A0
25 mM Mg2+
0.0026
-
geranyl diphosphate
D4N3A1
25 mM Mg2+
0.018
-
geranyl diphosphate
Cereus peruvianus
-
pH 6.6, 30C
0.06
-
Mg2+
Cereus peruvianus
-
pH 6.6, 30C
0.33
-
Mg2+
-
pH 7.4, 20C
0.346
-
Mg2+
D4N3A0
0.05 mM geranyl diphosphate
0.891
-
Mg2+
D4N3A1
0.05 mM geranyl diphosphate
0.0056
-
Mn2+
Cereus peruvianus
-
pH 6.6, 30C
0.0266
-
Mn2+
D4N3A1
0.05 mM geranyl diphosphate
0.0282
-
Mn2+
D4N3A0
0.05 mM geranyl diphosphate
0.045
-
Mn2+
-
pH 7.4, 20C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.014
-
geranyl diphosphate
D4N3A1
-
0.044
-
geranyl diphosphate
D4N3A0
-
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
5.6
-
geranyl diphosphate
D4N3A1
-
10850
21
-
geranyl diphosphate
D4N3A0
-
10850
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.0000067
-
-
protein represents approximately 10% of the total cellular protein
0.0004
-
-
purified enzyme
0.013
-
D4N3A1
in the presence of Mg2+, 22% activity in the presence of Mn2+
0.039
-
D4N3A0
in the presence of Mg2+, 50% activity in the presence of Mn2+
additional information
-
-
microgramm emitted linalool per g fresh weight
additional information
-
-
the transformant strain with the linalool synthase encoding gene is able to produce wine in the same way as the industrial T73 strain except for the quality trait introduced. The Saccharomyces cerevisiae industrial wine strain expressing a plant monoterpene synthase has the potential to alter the monoterpene profile of wine
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.6
-
Cereus peruvianus
-
small scale assay at
6.9
-
Cereus peruvianus
-
large scale assay at
7
-
-
activity assay
7.2
-
-
assay at, recombinant enzyme
7.4
-
-
broad optimum
7.8
-
-
assay at
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.4
8.4
-
80% of maximal activity within this range
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
20
-
-
assay at
30
-
-
assay at, recombinant enzyme
30
-
Cereus peruvianus
-
small scale assay at
30
-
-
activity assay
34
-
Cereus peruvianus
-
large scale assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
expression in flower buds, not in open flowers
Manually annotated by BRENDA team
-
activity occurs during ripening
Manually annotated by BRENDA team
-
expression in days 1-3 of open flowers
Manually annotated by BRENDA team
-
monoterpenes are produced in unopened buds and in open flowers with a peak at 2-3 days of anthesis
Manually annotated by BRENDA team
-
expression mainly in epidermis
Manually annotated by BRENDA team
Cereus peruvianus
-
ripening, very low levels in green immature fruits, enzyme levels increase during fruit ripening
Manually annotated by BRENDA team
-
exocarp, activity occurs during ripening
Manually annotated by BRENDA team
-
highest expression level of LIS2
Manually annotated by BRENDA team
-
of flower buds and open flowers, expression mainly in epidermis
Manually annotated by BRENDA team
-
high enzyme activity, linalool is emitted
Manually annotated by BRENDA team
-
high enzyme activity, linalool is mostly converted to linalool oxide
Manually annotated by BRENDA team
-
very low expression level of LIS1
Manually annotated by BRENDA team
-
high enzyme activity, linalool is mostly converted to linalool oxide
Manually annotated by BRENDA team
-
highest expression level of LIS1
Manually annotated by BRENDA team
-
low enzyme expression
Manually annotated by BRENDA team
-
of open flowers, high expression level in the secretory zone, between the papillate epidermis and parenchyma cells, converging into the style as a central region of transmitting tissue
Manually annotated by BRENDA team
-
high expression level, in the transmitting tissue but not in the vascular system or the stylar epidermis
Manually annotated by BRENDA team
additional information
-
floral tissue-specific expression levels of LIS1 and LIS2, overview, no expression in vegetative tissues
Manually annotated by BRENDA team
additional information
-
tissue specific expression dependent on developmental stage of flowers, no activity in leaves, no expression in sepals
Manually annotated by BRENDA team
additional information
-
the monoterpene is emitted soon after its synthesis
Manually annotated by BRENDA team
additional information
-
no activity determinable in cultured cell
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
53000
-
Cereus peruvianus
-
gel filtration
54000
-
-
determined by SDS-PAGE
59200
-
-
predicted molecular mass
73000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
D4N3A0
x * 65000, SDS-PAGE
?
D4N3A1
x * 65000, SDS-PAGE
monomer
-
1 * 79000, SDS-PAGE
additional information
-
the enzyme contains the conserved DDXXD motif
additional information
-
the enzyme contains the conserved DDXXD motif
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
DTT is required for enzyme stability, in absence of DTT the purified enzyme loses 95% of its activity within 2 h at 4C
-
hexane and pentane stabilize the enzyme
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Ni2+ affinity chromatography, gel filtration
D4N3A0
Ni2+ affinity chromatography, gel filtration
D4N3A1
partially from fruits by anion exchange chromatography
Cereus peruvianus
-
native enzyme 26fold from stigmata of freshly opened flowers by anion exchange and hydroxyapatite chromatography to over 95% purity
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
transient expression in Nicotiana benthamiana, His-tagged version expressed in Escherichia coli
D4N3A0
transient expression in Nicotiana benthamiana, His-tagged version expressed in Escherichia coli
D4N3A1
cloning in a binary vector for introduction into Agrobacterium tumefaciens strain LBA4404
-
Escherichia coli strain DH5alpha is used as the strain for cloning experiments and plasmid amplification. Saccharomyces cerevisiae wine strain T73-4 is used for functional expression of plasmids bearing the expression cassette.
-
functional expression in transgenic Petunia hybrida plants
-
gene LIS2, partial genomic library construction, DNA sequence determination and analysis, promoter sequence analysis, gene structure
-
partial protein sequencing and cDNA library construction, DNA and amino acid determination and analysis
-
partial genomic library construction, DNA sequence determination and analysis, promoter sequence analysis, gene structure
-
cDNA from strawberry with plastid targeting and a synthetic intron is placed under the control of the wound inducible proteinase inhibitor 2 (PI2) promoter from potato. The construct is transformed to Arabidopsis thaliana ecotype Columbia 0
Fragaria sp.
-
into the pNZ8150 vector for expression in Lactococcus lactis
-
partial genomic library construction, DNA sequence determination and analysis, gene structure
-
His-tagged version expressed in Escherichia coli; His-tagged version expressed in Escherichia coli
C0KWV5, C0KWV7, -
His-tagged version expressed in Escherichia coli
C0KWV3, -
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
construction of transgenic Petunia hybrida plants from wild-type W115 expressing Clarkia breweri LIS in all tissues with enantio-specific formation of (S)-linalool, which is converted to non-volatile beta-D-glucopyranoside by an endogenous glucosyltransferase, in leaves, sepals, corolla, stem, and ovary, but not in nectaris, roots, pollen, and style, plants show also increased alpha-terpineol levels
additional information
-
construction of transgenic tomato plants using the Agrbacterium tumefaciens transfection system, enzyme expression under control of a tomato-late-ripening-specific E8 promoter leads to accumulation of S-linalool and 8-hydroxylinalool in ripening fruits, volatile profiles of wild-type Lycopersicon esculentum plants and transgenic plants expressing LIS
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
biotechnology
-
the enzyme can be used to modify the flavor/nuritional value of vegetables, e.g. tomato fruits, by enzyme expression in transgenic plants
biotechnology
-
biotechnological potential of the engineered wine yeast to modify the sensorial qualities of wine
nutrition
-
the enzyme can be used to modify the flavor/nuritional value of vegetables, e.g. tomato fruits, by enzyme expression in transgenic plants
agriculture
Fragaria sp.
-
putative relevance for the engineering of indirect plant defence