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Information on EC 4.2.3.26 - R-linalool synthase
for references in articles please use BRENDA:EC4.2.3.26
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IUBMB Comments
Geranyl diphosphate cannot be replaced by isopentenyl diphosphate (3-methylbut-3-en-1-yl diphosphate), prenyl diphosphate, farnesyl diphosphate or geranylgeranyl diphosphate as substrate . Requires Mg2+ or Mn2+ for activity. Unlike many other monoterpene synthases, only a single product, (3R)-linalool, is formed.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
- 4.2.3.26
- flowers
- synthases
-
terpene
-
monoterpene
- s-linalool
-
scent
-
trichomes
-
farnesyl
-
enantiomer
- wounding
showSynonyms
lemts1, (r)-linalool synthase, r-linalool synthase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(R)-linalool synthase
Agrped1_689671
-
gene name, bifunctional linalool/nerolidol synthase is also able to convert farnesyl diphosphate into nerolidol
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + H2O = (3R)-linalool + diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
(3R)-linalool biosynthesis, linalool biosynthesis I
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [(3R)-linalool-forming]
Geranyl diphosphate cannot be replaced by isopentenyl diphosphate (3-methylbut-3-en-1-yl diphosphate), prenyl diphosphate, farnesyl diphosphate or geranylgeranyl diphosphate as substrate [1]. Requires Mg2+ or Mn2+ for activity. Unlike many other monoterpene synthases, only a single product, (3R)-linalool, is formed.
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CAS REGISTRY NUMBER
COMMENTARY
254993-26-5
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
farnesyl diphosphate
(E)-nerolidol + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
-
Substrates: Agrped1_689671 is a bifunctional enzyme, which is also able to convert farnesyl diphosphate into nerolidol. Agrped1_689675 is a monofunctional linalool synthase
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: the bifunctional enzyme is also able to convert farnesyl diphosphate into nerolidol
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
B5H117
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: the bifunctional enzyme is also able to convert farnesyl diphosphate into nerolidol
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
B5H117
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
(3R)-linalool + diphosphate
Substrates: -
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
Mg2+
the alpha-domain contains two conserved metal-ion coordination motifs (84DEXXD88 and 219NSE227)
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
EDTA
-
up to 95% loss of activity, isoenzyme QH1, full reactivation by 10 mM Mg2+
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
expression in leaves is induced by spider mite-infestation and wounding
-
additional information
-
expression in leaves is induced by spider mite-infestation and wounding
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0038
geranyl diphosphate
-
37°C, pH not specified in the publication, Agrped1_689675, monofunctional linalool synthase
0.0067
geranyl diphosphate
37°C, pH not specified in the publication
0.00911
geranyl diphosphate
pH 7.5, 37°C, cultivar Jinxuan
0.034
geranyl diphosphate
pH 7.5, 37°C, cultivar Lingtoudancong
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000436
geranyl diphosphate
pH 7.5, 37°C, cultivar Jinxuan
0.0000731
geranyl diphosphate
pH 7.5, 37°C, cultivar Lingtoudancong
0.0083
geranyl diphosphate
37°C, pH not specified in the publication
0.1
geranyl diphosphate
-
37°C, pH not specified in the publication, Agrped1_689675, monofunctional linalool synthase
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00212
geranyl diphosphate
pH 7.5, 37°C, cultivar Lingtoudancong
0.00479
geranyl diphosphate
pH 7.5, 37°C, cultivar Jinxuan
0.124
geranyl diphosphate
37°C, pH not specified in the publication
26.3
geranyl diphosphate
-
37°C, pH not specified in the publication, Agrped1_689675, monofunctional linalool synthase
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cultivars of Jinxuan and cultivar Lingtoudancong
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
stress-responsive genes, which prompts the accumulation of (R)-linalool under stresses
evolution
phylogenetic analysis indicates clear divergence among the 35 plant enzymes (4 nerolidol synthases, 9 linalool synthases, and 22 linalool/nerolidol synthases), 1 bacterial linalool synthase (D5SL78), and 9 fungal enzymes (linalool/nerolidol synthases and linalool synthases)
evolution
-
phylogenetic analysis indicates clear divergence among the 35 plant enzymes (4 nerolidol synthases, 9 linalool synthases, and 22 linalool/nerolidol synthases), 1 bacterial linalool synthase (D5SL78), and 9 fungal enzymes (linalool/nerolidol synthases and linalool synthases)
metabolism
-
the enzyme is essential for the production of major volatile organic compounds of champak flowers, (R)-linalool and linalool oxides
metabolism
most microbial TPSs have asparagine at the position corresponding to Agrocybe pediades Y299 and produce mainly cyclized products (delta-cadinene, 1,8-cineole, epi-cubebol, germacrene D, beta-barbatene, etc., cf. EC 4.2.3.26). Those producing linear products (linalool and nerolidol) typically have a bulky tyrosine
metabolism
linalool is abundant in tea leaves and contributes greatly to tea aroma. The two isomers of linalool, (R)-linalool and (S)-linalool, exist in tea leaves. (R)-linalool is the minor isomer in nine of Camellia sinensis var. sinensis cultivars. In teacultivars containing a lower ratio of (R)-linalool, the (R)-linalool synthase expression level is lower than that of (S)-linalool synthase
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). LLOS1_PICSI
627
0
71805
Swiss-Prot
other Location (Reliability: 2)
LNSA_STRCL
329
0
36397
Swiss-Prot
other Location (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
sequence contains a plastidial transit peptide
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystals of apo-enzyme in the presence of 10 mM Mg2+, to 1.99 A resolution
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Y299A
mutant yields long-chain (C15) linear or cyclic products (alpha-selinene, beta-selinene, and beta-elemene)
L72M
the variant has a linalool production level similar to native enzyme, but a lower nerolidol production (8% of total terpenoids production). The mutant enzyme prefers geranyl diphosphate over farnesyl diphosphate
V214L
the variant has a relatively low linalool titre compared to the native enzyme but the relative nerolidol production is even lower (less than 2 %). The mutant enzyme prefers geranyl diphosphate over farnesyl diphosphate
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
addition of bovine serum albumine, cytochrome c, or carbonic anhydrase stabilizes with concommittant increase in both Km- and kcat-value
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
a stress-free linalool-producing Saccharomyces cerevisiae cell factory is constructed by the combinational regulation of linalool synthase and farnesyl diphosphate synthase instead of multienzyme overexpression. Expression enhancement of linalool synthase (t67OMcLISE343D/E352H) is achieved by the addition of an N-terminal SKIK tag
expression in Escherichia coli Bl21-Gold DE3
GFP fusion protein CsRLIS-GFP is expressed in Arabidopsis protoplasts
into the pET32-a vector for expression in Escherichia coli BL21DE3 cells
linalool/nerolidol synthase (bLinS) from Streptomyces clavuligerus is a bifunctional enzyme, producing linalool as well as the sesquiterpenoid nerolidol when expressed in engineered Escherichia coli harbouring a precursor terpenoid pathway such as the mevalonate (MVA) pathway
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the expression level is increased during the tea manufacturing processes
the expression level of linalool synthase is successfully enhanced by introducing a N-terminal SKIK tag, which improves linalool production by 3.3fold
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RENATURED/Commentary
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
B5H117
linalool production utilizing two-phase cultivation system in Pantoea ananatis. Coexpression of the mutated farnesyl diphosphate synthase gene from Escherichia coli along with the linalool synthase gene improves linalool production. In order to prevent volatilization and cell toxicity of linalool, two phase cultivation with isopropyl myristate is done, which has positive effects on linalool production. 3.71 g/l (R)-linalool is produced from 60.0 g/l glucose in Pantoea ananatis
synthesis
optimised isopentenol utilization pathway to produce linalool using an integrated approach, combining protein engineering with flux control to improve titres and product purity in Escherichia coli. The residues L72 and V214 are important for geranyl diphosphate or farnesyl diphosphate substrate selection by the enzyme. Their exchange for bulkier residues results in enzyme variants with reduced nerolidol production. The isopentenol utilization pathway uses isoprenol and prenol to produce linalool in only five steps, and adjusting substrate concentration directs the flux towards monoterpenoids. Plasmid, inducer and strain optimisations further increased linalool titres
synthesis
linalool synthases are indispensable for the biosynthesis of linalool, an important fragrance used in 60-80% cosmetic and personal care products
synthesis
-
linalool synthases are indispensable for the biosynthesis of linalool, an important fragrance used in 60-80% cosmetic and personal care products
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Jia, J.W.; Crock, J.; Lu, S.; Croteau, R.; Chen, X.Y.
(3R)-Linalool synthase from Artemisia annua L.: cDNA isolation, characterization, and wound induction
Arch. Biochem. Biophys.
372
143-149
1999
Artemisia annua
brenda
Crowell, A.L.; Williams, D.C.; Davis, E.M.; Wildung, M.R.; Croteau, R.
Molecular cloning and characterization of a new linalool synthase
Arch. Biochem. Biophys.
405
112-121
2002
Mentha aquatica var. citrata (Q8H2B4)
brenda
van Schie, C.C.; Haring, M.A.; Schuurink, R.C.
Tomato linalool synthase is induced in trichomes by jasmonic acid
Plant Mol. Biol.
64
251-263
2007
Solanum lycopersicum (Q1XBU5), Solanum lycopersicum
brenda
Dhandapani, S.; Jin, J.; Sridhar, V.; Sarojam, R.; Chua, N.; Jang, I.
Integrated metabolome and transcriptome analysis of Magnolia champaca identifies biosynthetic pathways for floral volatile organic compounds
BMC Genomics
18
463
2017
Magnolia champaca
brenda
Pragadheesh, V.S.; Chanotiya, C.S.; Rastogi, S.; Shasany, A.K.
Scent from Jasminum grandiflorum flowers Investigation of the change in linalool enantiomers at various developmental stages using chemical and molecular methods
Phytochemistry
140
83-94
2017
Jasminum grandiflorum
brenda
Adal, A.M.; Sarker, L.S.; Malli, R.P.N.; Liang, P.; Mahmoud, S.S.
RNA-Seq in the discovery of a sparsely expressed scent-determining monoterpene synthase in lavender (Lavandula)
Planta
249
271-290
2019
Lavandula x intermedia (A0A2Z4XFW0)
brenda
Rehka, T.; Sharma, D.; Lin, F.; Choong, Y.K.; Lim, C.; Jobichen, C.; Zhang, C.
Structural understanding of fungal terpene synthases for the formation of linear or cyclic terpene products
ACS Catal.
13
4949-4959
2023
Agrocybe pediades (A0A8H4VHP2)
brenda
Ferraz, C.A.; Leferink, N.G.H.; Kosov, I.; Scrutton, N.S.
Isopentenol utilization pathway for the production of linalool in Escherichia coli using an improved bacterial linalool/nerolidol synthase
ChemBioChem
22
2325-2334
2021
Streptomyces clavuligerus (D5SL78)
brenda
Zhang, C.; Chen, X.; Lee, R.; Rehka, T.; Maurer-Stroh, S.; Rhl, M.
Bioinformatics-aided identification, characterization and applications of mushroom linalool synthases
Commun. Biol.
4
223
2021
Cyclocybe aegerita (A0A872TMX7), Agrocybe pediades
brenda
Zhou, Y.; Deng, R.; Xu, X.; Yang, Z.
Enzyme catalytic efficiencies and relative gene expression levels of (R)-linalool synthase and (S)-linalool synthase determine the proportion of linalool enantiomers in Camellia sinensis var. sinensis
J. Agric. Food Chem.
68
10109-10117
2020
Camellia sinensis var. sinensis (A0A7G8EIM4)
brenda
Zhou, P.; Du, Y.; Fang, X.; Xu, N.; Yue, C.; Ye, L.
Combinatorial modulation of linalool synthase and farnesyl diphosphate synthase for linalool overproduction in Saccharomyces cerevisiae
J. Agric. Food Chem.
69
1003-1010
2021
Mentha aquatica var. citrata (Q8H2B4)
brenda
Hoshino, Y.; Moriya, M.; Matsudaira, A.; Katashkina, J.I.; Nitta, N.; Nishio, Y.; Usuda, Y.
Stereospecific linalool production utilizing two-phase cultivation system in Pantoea ananatis
J. Biotechnol.
324
21-27
2020
Streptomyces clavuligerus (B5H117)
brenda
EXTERNAL LINKS (specific for EC-Number 4.2.3.26)
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