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geranyl diphosphate
gamma-terpinene + diphosphate
geranyl diphosphate + H2O
gamma-terpinene + diphosphate
Substrates: -
Products: 63% sabinene, 21% gamma-terpinene, 7% terpinolene, 6.5% limonene, and 2.5% myrcene
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neryl diphosphate
gamma-terpinene + diphosphate
-
Substrates: -
Products: 75% gamma-terpinene, 20% alpha-thujene, 5% alpha-terpineol, partially purified enzyme
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additional information
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geranyl diphosphate

gamma-terpinene + diphosphate
Substrates: -
Products: -
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geranyl diphosphate
gamma-terpinene + diphosphate
Substrates: -
Products: plus small amounts of alpha-pinene, limonene
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geranyl diphosphate
gamma-terpinene + diphosphate
Substrates: -
Products: -
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geranyl diphosphate
gamma-terpinene + diphosphate
Substrates: -
Products: 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
-
Substrates: -
Products: -
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
Substrates: -
Products: -
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geranyl diphosphate
gamma-terpinene + diphosphate
Substrates: -
Products: 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
Substrates: -
Products: -
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
Substrates: -
Products: -
?
geranyl diphosphate
gamma-terpinene + diphosphate
R4JHV6
Substrates: -
Products: plus minor products such as alpha-terpinene and alpha-thujene
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geranyl diphosphate
gamma-terpinene + diphosphate
Substrates: -
Products: plus minor products alpha-thujene, alpha-pinene, sabinene, beta-myrcene, alpha-terpinene
?
geranyl diphosphate
gamma-terpinene + diphosphate
-
Substrates: -
Products: 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
-
Substrates: -
Products: 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
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geranyl diphosphate
gamma-terpinene + diphosphate
-
Substrates: -
Products: -
?
geranyl diphosphate
gamma-terpinene + diphosphate
Substrates: -
Products: -
?
geranyl diphosphate
gamma-terpinene + diphosphate
Substrates: -
Products: -
?
additional information

?
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Substrates: product identification and quantification by GC-MS analysis
Products: -
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additional information
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Substrates: product identification and quantification by GC-MS analysis
Products: -
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additional information
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Substrates: GC-MS analysis of reaction product
Products: -
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additional information
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Substrates: GC-MS analysis of reaction product
Products: -
?
additional information
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Substrates: no substrate farnesyl diphosphate
Products: -
?
additional information
?
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Substrates: product identification and quantification by GC-MS analysis
Products: -
?
additional information
?
-
Substrates: product identification and quantification by GC-MS analysis
Products: -
?
additional information
?
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Substrates: product identification and quantification by GC-MS analysis
Products: -
?
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evolution
gamma-terpinene synthase (TPS) belongs to the monoterpene cyclases family
metabolism
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the enzyme catalyzes the proposed first step of thymoquinone biosynthesis, the formation of gamma-terpinene from geranyl diphosphate (GDP)
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
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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 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
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
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enzyme NsTPS1 elucidates the first dedicated step in the biosynthesis of thymoquinone in Nigella sativa
physiological function
gamma-terpinene is not only a monoterpene with antioxidant and antibacterial activities but also acts as a precursor of p-cymene, carvacrol, and thymol. In addition, gamma-terpinene synthase plays an essential role in the conversion of terpinen-4-yl cation to gamma-terpinene. Silver nanoparticles (AgNPs) strongly affect the secondary metabolites in cell suspension cultures of Carum carvi. 50 mg/ml AgNPs increase p-cymene and carvone contents in comparison with the control. The exposure of plants to 100 mg/l AgNPs induces the production of thymol and carvacrol. The application of AgNPs as an elicitor for 24 and 48 h significantly improves the essential oil composition and TPS2 gene expression in Carum carvi, overview
physiological function
the enzyme is responsible for the conversion of GPP into gamma-terpinene
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
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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
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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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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 gTRPS, DNA and amino acid sequence determination and analysis, sequence comparisons, quantitative real-time PCR enzyme expression analysis
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
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gene TPS1, DNA and amino acid sequence determination and analysis, codon-optimized gene, quantitative real-time PCR enzyme expression analysis, recombinant enzyme expression in Escherichia coli strains BL21(DE3) and CIBTS1756
gene TvTPS, DNA and amino acid sequence determination and analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21 CodonPlus
NsTPS1, cloning from seeds and functional recombinant expression in Escherichia coli
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real-time PCR enzyme expression analysis
expression in Escherichia coli

expression in Escherichia coli
expression in Escherichia coli
real-time PCR enzyme expression analysis

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real-time PCR enzyme expression analysis
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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 x 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 vulgare (E2E2P0), Origanum majorana
-
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
Dehghani-Aghchekohal, Z.; Omidi, M.; Azizinezhad, R.; Etminan, A.
Stimulation of secondary metabolites and gamma-terpinene synthase by silver nanoparticles in callus cultures of Carum carvi
Appl. Biochem. Biotechnol.
194
3228-3241
2022
Carum carvi (A0A8A9RYM4)
brenda
Elyasi, R.; Majdi, M.; Krause, S.T.; Kuecuekay, N.; Azizi, A.; Degenhardt, J.
Identification and functional characterization of a gamma-terpinene synthase in Nigella sativa L (black cumin)
Phytochemistry
202
113290
2022
Nigella sativa
brenda
Qi, C.; Zhao, H.; Li, W.; Li, X.; Xiang, H.; Zhang, G.; Liu, H.; Wang, Q.; Wang, Y.; Xian, M.; Zhang, H.
Production of gamma-terpinene by metabolically engineered Escherichia coli using glycerol as feedstock
RSC Adv.
8
30851-30859
2018
Thymus vulgaris (A0A0M3Q1Q3)
brenda