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Information on EC 4.2.3.144 - geranyllinalool synthase
for references in articles please use BRENDA:EC4.2.3.144
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EC Tree 4 Lyases
4.2 Carbon-oxygen lyases
4.2.3 Acting on phosphates
4.2.3.144 geranyllinalool synthase
IUBMB Comments
The enzyme is a component of the herbivore-induced indirect defense system. The product, (E,E)-geranyllinalool, is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT), which is released by many plants in response to damage.
The enzyme appears in viruses and cellular organisms
- 4.2.3.144
- synthases
-
diterpene
-
herbivore
-
sesquiterpene
-
terpenoids
- jasmonate
-
angiosperm
-
pollinators
- alamethicin
- ent-kaurene
-
insect-induced
-
plant-plant
-
orchid
- limonene
- attenuata
- agriculture
showSynonyms
tps-e/f, tps46, geranyllinalool synthase, slgls, nagls, terpene synthase tps4, tps04/ges, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
At1g61120
geranyllinalool synthase
GES
GLS
terpene synthase TPS4
TPS-e/f
TPS04/GES
TPS46
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranylgeranyl diphosphate + H2O = (6E,10E)-geranyllinalool + diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
geranylgeranyl diphosphate diphosphate-lyase ((E,E)-geranyllinalool-forming)
The enzyme is a component of the herbivore-induced indirect defense system. The product, (E,E)-geranyllinalool, is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT), which is released by many plants in response to damage.
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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
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
Substrates: reaction of EC 4.2.3.48
Products: -
Products: -
?
(2E,6E)-farnesyl diphosphate + H2O
trans-nerolidol + diphosphate
Substrates: -
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
Substrates: preferred substrate
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
Substrates: the product (E,E)-geranyllinalool is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) that is released by many plants in response to herbivory and may help to attract predators to combat the herbivores
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
Substrates: no activity with geranyl diphosphate or farnesyl diphosphate
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
Substrates: the product (E,E)-geranyllinalool is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) that is released by many plants in response to herbivory and may help to attract predators to combat the herbivores
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
Substrates: no activity with geranyl diphosphate or farnesyl diphosphate
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
Substrates: -
Products: additional products are + linalool + (E)-nerolidol. Products are precursors of (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene
Products: additional products are + linalool + (E)-nerolidol. Products are precursors of (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene
?
additional information
?
-
Substrates: the partially purified LnTPS3 protein catalyzes the formation of geranyllinalool from geranylgeranyl diphosphate (GGPP) and trans-nerolidol from eeFPP, GC-MS analysis of reaction products. In absence of functional LnTPS3, no trans-geranyllinalool and trans-nerolidol synthase activities are detected. No activity with geranyl diphosphate
Products: -
Products: -
?
additional information
?
-
-
Substrates: the partially purified LnTPS3 protein catalyzes the formation of geranyllinalool from geranylgeranyl diphosphate (GGPP) and trans-nerolidol from eeFPP, GC-MS analysis of reaction products. In absence of functional LnTPS3, no trans-geranyllinalool and trans-nerolidol synthase activities are detected. No activity with geranyl diphosphate
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme NaGLS is not active with geranyl diphosphate and farnesyl diphosphate, GC-MS analysis of compounds
Products: -
Products: -
?
additional information
?
-
-
Substrates: enzyme NaGLS is not active with geranyl diphosphate and farnesyl diphosphate, GC-MS analysis of compounds
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme SlTPS46 shows no activity with geranyl diphospate, GC-MS analysis of compounds
Products: -
Products: -
?
additional information
?
-
-
Substrates: enzyme SlTPS46 shows no activity with geranyl diphospate, GC-MS analysis of compounds
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
(2E,6E)-farnesyl diphosphate + H2O
(3S,6E)-nerolidol + diphosphate
Substrates: reaction of EC 4.2.3.48
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(6E,10E)-geranyllinalool + diphosphate
Substrates: -
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
Substrates: the product (E,E)-geranyllinalool is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) that is released by many plants in response to herbivory and may help to attract predators to combat the herbivores
Products: -
Products: -
?
geranylgeranyl diphosphate + H2O
(E,E)-geranyllinalool + diphosphate
Substrates: the product (E,E)-geranyllinalool is a precursor to the volatile compound 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) that is released by many plants in response to herbivory and may help to attract predators to combat the herbivores
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0637
(2E,6E)-farnesyl diphosphate
pH and temperature not specified in the publication
0.0187
geranylgeranyl diphosphate
pH and temperature not specified in the publication
0.0315
geranylgeranyl diphosphate
pH and temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.43
(2E,6E)-farnesyl diphosphate
pH and temperature not specified in the publication
6.85
geranylgeranyl diphosphate
pH and temperature not specified in the publication
7.53
geranylgeranyl diphosphate
pH and temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6.75
(2E,6E)-farnesyl diphosphate
pH and temperature not specified in the publication
239.05
geranylgeranyl diphosphate
pH and temperature not specified in the publication
366.3
geranylgeranyl diphosphate
pH and temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
expression is higher in young leaves compared to old ones
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additional information
traces of geranylgeranyl diphosphate in all tissues, and small amounts of the C16-homoterpene 4,8,12-trimethyltridacan-1,3,7,11-tetraene (TMTT), which is derived from geranyllinalool
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additional information
-
traces of geranylgeranyl diphosphate in all tissues, and small amounts of the C16-homoterpene 4,8,12-trimethyltridacan-1,3,7,11-tetraene (TMTT), which is derived from geranyllinalool
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
additional information
the enzyme is not localized to the plastids
-
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additional information
-
the enzyme is not localized to the plastids
-
brenda
additional information
-
the enzyme is not localized to the plastids
-
-
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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
malfunction
metabolism
physiological function
additional information
evolution
SlGLS, NaGLS, AtGLSs, and several other GLSs come from different eudicot families and constitute a separate branch of the TPS-e/f clade that diverged from kaurene synthases, also in the TPS-e/f clade, before the gymnosperm-angiosperm split. The early divergence of this branch and the GLS activity of genes in this branch in diverse eudicot families suggest that GLS activity encoded by these genes predates the angiosperm-gymnosperm split
evolution
SlGLS, NaGLS, AtGLSs, and several other GLSs come from different eudicot families and constitute a separate branch of the TPS-e/f clade that diverged from kaurene synthases, also in the TPS-e/f clade, before the gymnosperm-angiosperm split. The early divergence of this branch and the GLS activity of genes in this branch in diverse eudicot families suggest that GLS activity encoded by these genes predates the angiosperm-gymnosperm split
evolution
geranyllinalool synthase activity is the likely ancestral function in angiosperms of genes belonging to an ancient TPS-e/f subclade that diverged from the kaurene synthase gene lineages before the split of angiosperms and gymnosperms. The geranyllinalool synthase subclade diverged from the rest of the TPS genes in clade e/f before the split of the gymnosperm and angiosperm lineages, enzymes encoded by genes in this subclade have only been characterized from eudicot species. Laurus nobilis also has a gene belonging to the geranyllinalool synthase subclade of TPS clade e/f and the enzyme encoded by this gene is an active geranyllinalool synthase. Geranyllinalool might have been one of the first specialized metabolites to have evolved from early stages in the evolution of the TPS gene family in plants. Phylogenetic analysis, unrooted tree
malfunction
transgenic Arabidopsis lines carrying T-DNA insertions in the TPS04 locus are deficient in (E,E)-geranyllinalool and 4,8,12-trimethyl-1,3,7,11-tridecatetraene synthesis
malfunction
the tps4 knockout mutant completely lacks induced emission of 4,8,12-trimethyl-1,3,7,11-tridecatetraene but is capable of beta-ionone and alpha-farnesene production, demonstrating that TPS4 is specifically involved in 4,8,12-trimethyl-1,3,7,11-tridecatetraene formation
malfunction
-
the tps4 knockout mutant completely lacks induced emission of 4,8,12-trimethyl-1,3,7,11-tridecatetraene but is capable of beta-ionone and alpha-farnesene production, demonstrating that TPS4 is specifically involved in 4,8,12-trimethyl-1,3,7,11-tridecatetraene formation
-
malfunction
-
transgenic Arabidopsis lines carrying T-DNA insertions in the TPS04 locus are deficient in (E,E)-geranyllinalool and 4,8,12-trimethyl-1,3,7,11-tridecatetraene synthesis
-
metabolism
the terpene synthase (TPS) catalyzes a two-step reaction in which carbocation formation of the C20 precursor geranylgeranyl diphosphate (GGPP) is followed by an allylic rearrangement that results in the production of the tertiary alcohol geranyllinalool, which is the precursor for biosynthesis of (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT
metabolism
the terpene synthase (TPS) catalyzes a two-step reaction in which carbocation formation of the C20 precursor geranylgeranyl diphosphate (GGPP) is followed by an allylic rearrangement that results in the production of the tertiary alcohol geranyllinalool, which is the precursor for biosynthesis of (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT
physiological function
the enzyme is specifically involved in 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) formation. Induced TMTT production in Arabidopsis is a by-product of activated jasmonic acid signaling, rather than an effective defense response that contributes to resistance against Pseudomonas syringae
physiological function
contrary to wild-type, transgenic Lotus japonicus plants expressing isoform TPS2 produce (E,E)-geranyllinalool and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene. Transgenic Nicotiana tabacum expressing isoform TPS2 produces (E,E)-geranyllinalool but not (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene. In olfactory assays, the generalist predatory mite Neoseiulus californicus but not the specialist Phytoseiulus persimilis is attracted to uninfested, transgenic Lotus japonicus plants expressing TPS2 over wild-type plants. The specialist Phytoseiulus persimilis is more strongly attracted by the transgenic plants infested with spider mites than by infested wild-type plants
physiological function
GC-MS analysis of terpene volatiles induced by alamethicin treatment, overview
physiological function
GC-MS analysis of terpene volatiles induced by alamethicin treatment, overview
physiological function
-
the enzyme is specifically involved in 4,8,12-trimethyl-1,3,7,11-tridecatetraene (TMTT) formation. Induced TMTT production in Arabidopsis is a by-product of activated jasmonic acid signaling, rather than an effective defense response that contributes to resistance against Pseudomonas syringae
-
additional information
volatile profiles in leaves, flowers, fruits, and roots in male and female Laurus nobilis plants, overview. The biggest gender differences are observed in the flowers, where female flowers have predominantly monoterpenes as well as eugenol and methyleugenol, whereas male flowers contain mostly sesquiterpenes and benzaldehyde
additional information
-
volatile profiles in leaves, flowers, fruits, and roots in male and female Laurus nobilis plants, overview. The biggest gender differences are observed in the flowers, where female flowers have predominantly monoterpenes as well as eugenol and methyleugenol, whereas male flowers contain mostly sesquiterpenes and benzaldehyde
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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). GES_ARATH
877
0
101895
Swiss-Prot
Secretory Pathway (Reliability: 4)
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) LnTPS3 does not bind to the nickel-agarose column, and is instead partially purified by anion exchange chromatography and desalting gel filtration to about 5% purity
recombinant N-terminally His-tagged SlTPS46 from Escherichia coli by nickel affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene LnTPS3, sequence comparisons and phylogenetic analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) from expression vector pEXP5-CT/TOPO TA
gene NaTPS46, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, recombinant expression of N-terminally His-tagged enzyme in Escherichia coli
gene SlTPS46 encoding SlGLS, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, recombinant expression of N-terminally His-tagged SlTPS46 in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
highly coordinated herbivore-induced expression of geranyllinalool synthase with CYP82G1 (At3g25180, a cytochrome P450 monooxygenase of the Arabidopsis CYP82 family, is responsible for the breakdown of the C20-precursor (E,E)-geranyllinalool to the insect-induced C16-homoterpene (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene (TMTT)) in leaves depending on the F-box protein COI-1
is expressed in response to Pseudomonas syringae inoculation or intoxication of Arabidopsis leaves with copper sulfate
NaGLS is expressed constitutively, but the gene NaTPS46 can be induced in leaves with methyl jasmonate
no induction of the enzyme by the defense-suppressing mite line Tetranycus evansi Vicosa-1
TPS46 shows induction by alamethicin and methyljasmonate treatment, induction by defense-inducing spider mite line Tetranycus urticae Santpoort-2
transcription is upregulated under conditions that induce (E,E)-geranyllinalool and 4,8,12-trimethyltrideca-1,3,7,11-tetraene synthesis, including infestation of plants with larvae of the moth Plutella xylostella and treatment with the fungal peptide alamethicin or the octadecanoid mimic coronalon. Induction requires jasmonic acid but is independent from salicylic acid or ethylene
is expressed in response to Pseudomonas syringae inoculation or intoxication of Arabidopsis leaves with copper sulfate
is expressed in response to Pseudomonas syringae inoculation or intoxication of Arabidopsis leaves with copper sulfate
-
-
transcription is upregulated under conditions that induce (E,E)-geranyllinalool and 4,8,12-trimethyltrideca-1,3,7,11-tetraene synthesis, including infestation of plants with larvae of the moth Plutella xylostella and treatment with the fungal peptide alamethicin or the octadecanoid mimic coronalon. Induction requires jasmonic acid but is independent from salicylic acid or ethylene
transcription is upregulated under conditions that induce (E,E)-geranyllinalool and 4,8,12-trimethyltrideca-1,3,7,11-tetraene synthesis, including infestation of plants with larvae of the moth Plutella xylostella and treatment with the fungal peptide alamethicin or the octadecanoid mimic coronalon. Induction requires jasmonic acid but is independent from salicylic acid or ethylene
-
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
contrary to wild-type, transgenic Lotus japonicus plants expressing isoform TPS2 produce (E,E)-geranyllinalool and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene. Transgenic Nicotiana tabacum expressing isoform TPS2 produces (E,E)-geranyllinalool but not (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene. In olfactory assays, the generalist predatory mite Neoseiulus californicus but not the specialist Phytoseiulus persimilis is attracted to uninfested, transgenic Lotus japonicus plants expressing TPS2 over wild-type plants. The specialist Phytoseiulus persimilis is more strongly attracted by the transgenic plants infested with spider mites than by infested wild-type plants
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lee, S.; Badieyan, S.; Bevan, D.R.; Herde, M.; Gatz, C.; Tholl, D.
Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis
Proc. Natl. Acad. Sci. USA
107
21205-21210
2010
Arabidopsis thaliana (Q93YV0)
brenda
Attaran, E.; Rostas, M.; Zeier, J.
Pseudomonas syringae elicits emission of the terpenoid (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene in Arabidopsis leaves via jasmonate signaling and expression of the terpene synthase TPS4
Mol. Plant Microbe Interact.
21
1482-1497
2008
Arabidopsis thaliana (Q93YV0), Arabidopsis thaliana, Arabidopsis thaliana Heynh. (Q93YV0)
brenda
Herde, M.; Grtner, K.; Kllner, T.G.; Fode, B.; Boland, W.; Gershenzon, J.; Gatz, C.; Tholl, D.
Identification and regulation of TPS04/GES, an Arabidopsis geranyllinalool synthase catalyzing the first step in the formation of the insect-induced volatile C16-homoterpene TMTT
Plant Cell
20
1152-1168
2008
Arabidopsis thaliana (Q93YV0), Arabidopsis thaliana, Arabidopsis thaliana Columbia ecotype (Q93YV0)
brenda
Brillada, C.; Nishihara, M.; Shimoda, T.; Garms, S.; Boland, W.; Maffei, M.E.; Arimura, G.
Metabolic engineering of the C16 homoterpene TMTT in Lotus japonicus through overexpression of (E,E)-geranyllinalool synthase attracts generalist and specialist predators in different manners
New Phytol.
200
1200-1211
2013
Phaseolus lunatus (U5KL21)
brenda
Falara, V.; Alba, J.; Kant, M.; Schuurink, R.; Pichersky, E.
Geranyllinalool synthases in Solanaceae and other angiosperms constitute an ancient branch of diterpene synthases involved in the synthesis of defensive compounds
Plant Physiol.
166
428-441
2014
Nicotiana attenuata (A0A088DC07), Nicotiana attenuata, Solanum lycopersicum (K4BE78), Solanum lycopersicum
brenda
Yahyaa, M.; Matsuba, Y.; Brandt, W.; Doron-Faigenboim, A.; Bar, E.; McClain, A.; Davidovich-Rikanati, R.; Lewinsohn, E.; Pichersky, E.; Ibdah, M.
Identification, functional characterization, and evolution of terpene synthases from a basal dicot
Plant Physiol.
169
1683-1697
2015
Laurus nobilis (A0A0H4U599), Laurus nobilis
brenda
EXTERNAL LINKS (specific for EC-Number 4.2.3.144)
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