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Information on EC 4.2.3.114 - gamma-terpinene synthase
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4.2.3.114 gamma-terpinene synthaseIUBMB Comments
Isolated from Thymus vulgaris (thyme) [1,2], Citrus limon (lemon) , Citrus unshiu (satsuma) and Origanum vulgare (oregano) . Requires Mg2+. Mn2+ less effective. The reaction involves a 1,2-hydride shift. The 5-pro-S hydrogen of geranyl diphosphate is lost. Traces of several other monoterpenoids are formed in addition to gamma-terpinene.
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The enzyme appears in viruses and cellular organisms
Synonyms
gamma-terpinene synthase, tvtps, ostps24, ovtps2, clcts, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ClcTS
-
-
-
-
OvTPS2
-
-
-
-
TPS2
TvTPS2
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = gamma-terpinene + diphosphate
-
-
-
-
geranyl diphosphate = gamma-terpinene + diphosphate
ionization of geranyl diphosphate folded in left-handed helical form gives, by syn-isomerization, (3R)-linalyl diphosphate, which by rotation about C2-C3 provides the cisoid, anti-endo conformation. Ionization and cyclization of this bound intermediate yield the (4R)-alpha-terpinyl cation that, following the 1,2-hydride shift, affords the terpinen-4-yl cation. Loss of the (5S)-proton terminates the reaction to generate gamma-terpinene
-
geranyl diphosphate = gamma-terpinene + diphosphate
major products sabinene and gamma-terpinene are formed by a cyclization mechanism involving a 1,2-hydride shift in the alpha-terpinyl cation intermediate
geranyl diphosphate = gamma-terpinene + diphosphate
mechanism involves the cyclizazion of the acyclic precursor, loss of a proton from C5 to form the delta4 double bond, and a 1,2-hydride shift fom C4 to C8 to give gamma-terpinene
-
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase (cyclizing, gamma-terpinene-forming)
Isolated from Thymus vulgaris (thyme) [1,2], Citrus limon (lemon) [3], Citrus unshiu (satsuma) [4] and Origanum vulgare (oregano) [5]. Requires Mg2+. Mn2+ less effective. The reaction involves a 1,2-hydride shift. The 5-pro-S hydrogen of geranyl diphosphate is lost. Traces of several other monoterpenoids are formed in addition to gamma-terpinene.
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CAS REGISTRY NUMBER
COMMENTARY
68943-55-5
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate + H2O
gamma-terpinene + diphosphate
-
63% sabinene, 21% gamma-terpinene, 7% terpinolene, 6.5% limonene, and 2.5% myrcene
-
?
neryl diphosphate
gamma-terpinene + diphosphate
-
-
75% gamma-terpinene, 20% alpha-thujene, 5% alpha-terpineol, partially purified enzyme
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
products are 71.4% gamma-terpinene, with lower amounts of limonene (9.1%), alpha-pinene (5.6%), beta-pinene (4.7%), alpha-terpinolene (3.7%), alpha-thujene (2.5%), alpha-terpinene (1.7%), myrcene (0.9%), sabinene (0.4%) and a trace of p-cymene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
plus small amounts of alpha-pinene, limonene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
products are 80% gamma-terpinene and the minor products, alpha-thujene (7.2%), alpha-terpinene (6%), myrcene (2.6%), sabinene (1.3%), (+)-R-limonene (1.2%), alpha-pinene (1%) and alpha-phellandrene (0.8%), as well as trace amounts of p-cymene and beta-pinene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
plus minor products alpha-thujene, alpha-pinene, sabinene, beta-myrcene, alpha-terpinene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
R4JHV6
-
plus minor products such as alpha-terpinene and alpha-thujene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
-
ionization of geranyl diphosphate folded in left-handed helical form gives, by syn-isomerization, (3R)-linalyl diphosphate, which by rotation about C2-C3 provides the cisoid, anti-endo conformation. Ionization and cyclization of this bound intermediate yield the (4R)-alpha-terpinyl cation that, following the 1,2-hydride shift, affords the terpinen-4-yl cation. Loss of the (5S)-proton terminates the reaction to generate gamma-terpinene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
-
products are about 64% gamma-terpinen, 10% alpha-thujene, 4% myrcene, 4% alpha-terpinene, 2% limonene, 3% linalool, 2% terpinen-4-ol, 3% alpha-terpineol
-
?
additional information
?
-
product identification and quantification by GC-MS analysis
-
-
?
additional information
?
-
-
product identification and quantification by GC-MS analysis
-
-
?
additional information
?
-
no substrate farnesyl diphosphate
-
-
?
additional information
?
-
product identification and quantification by GC-MS analysis
-
-
?
additional information
?
-
product identification and quantification by GC-MS analysis
-
-
?
additional information
?
-
-
product identification and quantification by GC-MS analysis
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
Mg2+
or Mn2+, required. Optimum concentration of Mg2+ 0.025 mM, 44% of the activity wit Mn2+
Mn2+
or Mg2+, required. Mn2+ is preferred over Mg2+, optimum concentration 0.001 mM
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Dehydration
Effect of prolonged water stress on essential oil content, compositions and gene expression patterns of mono- and sesquiterpene synthesis in two oregano (Origanum vulgare L.) subspecies.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
six different variants of the gene are distinguishable according to sequence characteristics in intron 3, after comprehensive analysis in Origanum dubium, Origanum majorana, Origanum onites, and Origanum syriacum. The formation of characteristic essential oil compounds is associated with the presence of variants 1 and/or 3 and/or 4 in the gene. In plants lacking these variants, the compounds are completely absent or present in trace amounts only
UniProt
brenda
carvacrol-rich plant, cloning from chemically distinct Thymus caespititius plants
R4JHV6
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
additional information
-
GC-MS analysis of plant volatiles st different developmental plant stages and varieties, overview
brenda
additional information
GC-MS analysis of plant volatiles at different developmental plant stages and varieties, overview
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
in general, monoterpene synthases contain a transit peptide for translocation to plastids and sesquiterpene synthases are localized in the cytoplasm
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
additional information
physiological function
-
enzyme OsTPS24 is localized in chloroplasts and produced the monoterpene, gamma-terpinene. The amount of gamma-terpinene increased after jasmonate treatment. gamma-Terpinene has significant antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo), but it does not show significant antifungal activity against Magnaporthe oryzae. The antibacterial activity of gamma-terpinene against Xoo is caused by damage to bacterial cell membranes. These results suggest that gamma-terpinene plays an important role in jasmonate-induced resistance against Xoo, and that it functions as an antibacterial compound in rice plants
physiological function
The biosynthesis of gamma-terpinene, a precursor of the phenolic isomers thymol and carvacrol found in the essential oil from Thymus sp., is attributed to the activitiy of gamma-terpinene synthase (TvTPS)
physiological function
-
the monoterpene synthase activity is predominantly regulated at the level of transcription, and the phenolic monoterpene alcohol thymol is derived from gamma-terpinene, the product of a single monoterpene synthase. Terpene synthase expression levels directly control the composition of the essential oils. Proportion (%) changes of essential oil components in different varieties of Origanum majorana, GC-MS analysis of plant volatiles, overview
physiological function
the monoterpene synthase activity is predominantly regulated at the level of transcription, and the phenolic monoterpene alcohol thymol is derived from gamma-terpinene, the product of a single monoterpene synthase. Terpene synthase expression levels directly control the composition of the essential oils. Proportion (%) changes of essential oil components in different varieties of Origanum vulgare, GC-MS analysis of plant volatiles, overview
additional information
putative active site of TvTPS is deduced from its pronounced structural similarity to enzymes from other species of the Lamiaceae family involved in terpenoid biosynthesis
additional information
putative active site of TvTPS is deduced from its pronounced structural similarity to enzymes from other species of the Lamiaceae family involved in terpenoid biosynthesis
additional information
-
putative active site of TvTPS is deduced from its pronounced structural similarity to enzymes from other species of the Lamiaceae family involved in terpenoid biosynthesis
additional information
-
tissue-specific expression patterns of genes associated with the terpeniod biosynthesis in two oregano species Origanum vulgare and Origanum majorana, GC-MS analysis of plant volatiles, overview
additional information
tissue-specific expression patterns of genes associated with the terpeniod biosynthesis in two oregano species Origanum vulgare and Origanum majorana, GC-MS analysis of plant volatiles, overview
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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). GTPS3_THYCA
597
0
69183
Swiss-Prot
Chloroplast (Reliability: 2)
GTPSB_THYCA
597
0
69288
Swiss-Prot
Chloroplast (Reliability: 2)
GTPSC_THYCA
597
0
69296
Swiss-Prot
Chloroplast (Reliability: 3)
GTPS_CITLI
600
0
69522
Swiss-Prot
Chloroplast (Reliability: 4)
GTPS_ORIVU
594
0
69063
Swiss-Prot
Chloroplast (Reliability: 1)
TPS7_HEDCO
593
0
68541
Swiss-Prot
Chloroplast (Reliability: 3)
GTPS1_THYVU
542
0
63274
Swiss-Prot
other Location (Reliability: 3)
TPS17_SOLHA
554
0
64892
Swiss-Prot
other Location (Reliability: 2)
TPS17_SOLLC
554
0
64835
Swiss-Prot
other Location (Reliability: 2)
TPS26_MAIZE
627
0
70785
Swiss-Prot
Chloroplast (Reliability: 2)
S5Z6T7_9LAMI
596
0
68907
TrEMBL
Chloroplast (Reliability: 2)
S5ZYI9_9LAMI
596
0
68941
TrEMBL
Chloroplast (Reliability: 2)
S5ZIA8_9LAMI
596
0
69052
TrEMBL
Chloroplast (Reliability: 2)
A0A8A9RYM4_CARCB
64
0
7844
TrEMBL
Secretory Pathway (Reliability: 5)
S5YZ41_9LAMI
596
0
68947
TrEMBL
Chloroplast (Reliability: 2)
S5Z6T0_9LAMI
596
0
69026
TrEMBL
Chloroplast (Reliability: 2)
S5YT86_9LAMI
596
0
69019
TrEMBL
Chloroplast (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
96000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
dimer
overall structure of each TvTPS1 monomer comprises two alpha-helical domains: an N-terminal domain comprising an alpha/alpha barrel and a C-terminal orthogonal bundle domain, crystal structure analysis
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
homology modeling based on gamma-terpinene synthase from Origanum vulgare. Besides the aspartate-rich region DDxxD, the sites Asp452, Thr456 and Glu460 involved on stabilization of active site by Mg2+ cofactor are also conserved
R4JHV6
purified recombinant enzyme, sitting drop method, mixing of 400-600 nl of 10 mg/ml protein in 20 mM Tris-HCl, pH 7.8, 1 mM MgCl2, 4 mM DTT, with reservoir solution containing 0.2 M ammonium tartrate, pH 7.0, 20% w/v PEG 3350, in a 1:1 or 1:2 ratio, equilibration against 0.07 ml reservoir solution, 19°C, X-ray diffraction structure determination and analysis at 1.65-1.90 A resolution, two molecules (monomers A and B) in the asymmetric unit, molecular replacement using the crystal structure of (4S)-limonene synthase from Mentha spicata, PDB ID 2ong, model building
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D356A
site-directed mutagenesis, the activity of the mutant is completely abolished
T565A
site-directed mutagenesis, the mutation results in a 82% decrease in activity compared to wild-type
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
addition of either 20% glycerol or 1 mM substrate does not significantly improve stability
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0°C, 40 mM sodium phosphate, 5 mM MgCl2, 0.5 mM dithioerythritol, loss of 60% of activity within 1 week
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21 CodonPlus by nickel affinity chromatography, ultrafiltration, and gel filtration
recombinant His-tagged recombinant TPS24 lacking the putative chloroplast transit sequence from Escherichia coli by nickel affinity chromatography and dialysis
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
gene CitMTSL61, HA-tag and a start codon are introduced to the synthetic gene before the arginine pair at position R56-R57 by using PCR to create gTerpS, recombinant overexpression of the codon-optimized gTerpS from plasmid pHHO5 in Aspergillus nidulans strain A772 resulting in production of gamma-terpinene, and expression of codon-optimized gTerpS in Saccharomyces cerevisiae strain H2802 from vector B1181. Real-time quantitative reverse transcription PCR expression analysis. Aspergillus nidulans is capable of heterologous terpene production and thus has potential as a production host for industrially relevant compounds
gene OsTPS24, DNA and amino acid sequence determination and analysis, quantitative RT-PCR expression analysis, functional recombinant expression of His-tagged recombinant TPS24 lacking the putative chloroplast transit sequence in Escherichia coli, expression of GFP-tagged enzyme in Oryza sativa protoplasts chloroplasts
-
gene TvTPS, DNA and amino acid sequence determination and analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21 CodonPlus
real-time PCR enzyme expression analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
terpene synthase expression levels directly control the composition of the essential oil
the enzyme encoded by gene OsTPS24 is highly induced about 20fold by jasmonate, expression pattern, overview
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
recombinant expression in Aspergillus nidulans resulting in production of gamma-terpinene. Aspergillus nidulans is capable of heterologous terpene production and thus has potential as a production host for industrially relevant compounds, e.g. gamma-terpinene
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Wise, M.L.; Savage, T.J.; Katahira, E.; Croteau, R.
Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase
J. Biol. Chem.
273
14891-14899
1998
Salvia officinalis (O81193)
brenda
Lucker, J.; El Tamer, M.K.; Schwab, W.; Verstappen, F.W.; van der Plas, L.H.; Bouwmeester, H.J.; Verhoeven, H.A.
Monoterpene biosynthesis in lemon (Citrus limon). cDNA isolation and functional analysis of four monoterpene synthases
Eur. J. Biochem.
269
3160-3171
2000
Citrus limon (Q8L5K4)
brenda
LaFever, R.E.; Croteau, R.
Hydride shifts in the biosynthesis of the p-menthane monoterpenes alpha-terpinene, gamma-terpinene, and beta-phellandrene
Arch. Biochem. Biophys.
301
361-366
1993
Thymus vulgaris
brenda
Poulose, A.; Croteau, R.
gamma-Terpinene synthetase: A key enzyme in the biosynthesis of aromatic monoterpenes
Arch. Biochem. Biophys.
191
400-411
1978
Thymus vulgaris
brenda
Alonso, W.R.; Croteau, R.
Purification and characterization of the monoterpene cyclase gamma-terpinene synthase from Thymus vulgaris
Arch. Biochem. Biophys.
286
511-517
1991
Thymus vulgaris
brenda
Suzuki, Y.; Sakai, H.; Shimada, T.; Omura, M.; Kumazawa, S.; Nakayama, T.
Characterization of gamma-terpinene synthase from Citrus unshiu (Satsuma mandarin)
Biofactors
21
79-82
2004
Citrus unshiu (Q6F5H1), Citrus unshiu
brenda
Lukas, B.; Samuel, R.; Novak, J.
Oregano or marjoram? The enzyme gamma-terpinene synthase affects chemotype formation in the genus Origanum
Isr. J. Plant Sci.
58
211-220
2010
Origanum syriacum (G3LTY3)
-
brenda
Crocoll, C.; Asbach, J.; Novak, J.; Gershenzon, J.; Degenhardt, J.
Terpene synthases of oregano (Origanum vulgare L.) and their roles in the pathway and regulation of terpene biosynthesis
Plant Mol. Biol.
73
587-603
2010
Origanum vulgare (E2E2P0)
brenda
Mendes, M.D.; Barroso, J.G.; Oliveira, M.M.; Trindade, H.
Identification and characterization of a second isogene encoding alpha-terpinene synthase in Thymus caespititius
J. Plant Physiol.
171
1017-1027
2014
Thymus caespititius (A0A068EN29)
brenda
Lima, A.S.; Schimmel, J.; Lukas, B.; Novak, J.; Barroso, J.G.; Figueiredo, A.C.; Pedro, L.G.; Degenhardt, J.; Trindade, H.
Genomic characterization, molecular cloning and expression analysis of two terpene synthases from Thymus caespititius (Lamiaceae)
Planta
238
191-204
2013
Thymus caespititius (R4JHV6)
brenda
Rudolph, K.; Parthier, C.; Egerer-Sieber, C.; Geiger, D.; Muller, Y.A.; Kreis, W.; Mueller-Uri, F.
Expression, crystallization and structure elucidation of gamma-terpinene synthase from Thymus vulgaris
Acta Crystallogr. Sect. F
72
16-23
2016
Thymus vulgaris (A0A0M3Q1Q3), Thymus vulgaris (K9Y6Y9), Thymus vulgaris
brenda
Bromann, K.; Toivari, M.; Viljanen, K.; Ruohonen, L.; Nakari-Setaelae, T.
Engineering Aspergillus nidulans for heterologous ent-kaurene and gamma-terpinene production
Appl. Microbiol. Biotechnol.
100
6345-6359
2016
Citrus unshiu (Q6F5H0), Citrus unshiu
brenda
Jan, S.; Mir, J.; Shafi, W.; Faktoo, S.; Singh, D.; Wijaya, L.; Alyemeni, M.; Ahmad, P.
Divergence in tissue-specific expression patterns of genes associated with the terpeniod biosynthesis in two oregano species Origanum vulgare L., and Origanum majorana
Indust. Crops Prod.
123
546-555
2018
Origanum majorana, Origanum vulgare (E2E2P0)
-
brenda
Yoshitomi, K.; Taniguchi, S.; Tanaka, K.; Uji, Y.; Akimitsu, K.; Gomi, K.
Rice terpene synthase 24 (OsTPS24) encodes a jasmonate-responsive monoterpene synthase that produces an antibacterial gamma-terpinene against rice pathogen
J. Plant Physiol.
191
120-126
2016
Oryza sativa
brenda
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