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(3R)-linalyl diphosphate
terpinolene + diphosphate
-
-
products are 17% (-)-alpha-pinene, 9% beta-pinene, 3% camphene, 28% limonene, 9% terpinolene, 23% myrcene, 3% cis-ocimene, 13% trans-ocimene, products are 62% (+)-alpha-pinene, 6% camphene, 11% limonene, 7% terpinolene, 10% myrcene, 1% cis-ocimene, 4% trans-ocimene
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?
(3S)-linalyl diphosphate
terpinolene + diphosphate
-
-
products are 15% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 11% limonene, 6% terpinolene, 23% myrcene, 3% cis-ocimene, 8% trans-ocimene, products are 9% (+)-alpha-pinene, 9% camphene, 34% limonene, 28%% terpinolene, 11% myrcene, 2% cis-ocimene, 6% trans-ocimene
-
?
2 geranyl diphosphate
(+)-car-3-ene + terpinolene + 2 diphosphate
2 geranyl diphosphate
(-)-sabinene + terpinolene + 2 diphosphate
-
wild-type produces 1.3% (+)-car-3-ene, 44.7% (-)-sabinene, 35.9% terpinolene
-
?
geranyl diphosphate
terpinolene + diphosphate
neryl diphosphate
terpinolene + diphosphate
-
-
products are 14% (+)-alpha-pinene, 9% camphene, 62% limonene, 8% terpinolene, 6% myrcene, products are 18% (-)-alpha-pinene, 18% beta-pinene, 12% camphene, 42% limonene, 9% terpinolene, 9% myrcene
-
?
additional information
?
-
2 geranyl diphosphate
(+)-car-3-ene + terpinolene + 2 diphosphate
-
wild-type produces 46.2% (+)-car-3-ene, 8.8% (-)-sabinene, 29.7% terpinolene
-
?
2 geranyl diphosphate
(+)-car-3-ene + terpinolene + 2 diphosphate
-
wild-type produces 67.5% (+)-car-3-ene, 6.9% (-)-sabinene, 15.4% terpinolene
-
?
geranyl diphosphate
terpinolene + diphosphate
-
42% terpinolene, 18% (-)-alpha-pinene, 11% (-)-limonene, 10% (-)-beta-pinene plus several minor products
-
?
geranyl diphosphate
terpinolene + diphosphate
-
-
-
?
geranyl diphosphate
terpinolene + diphosphate
-
-
-
?
geranyl diphosphate
terpinolene + diphosphate
-
products are 39% (R)-(+)-limonene, 22% terpinolene, 16% (1R,5S)-(+)-camphene, 14% (1R,5R)-(+)-alpha-pinene, 8% betamyrcene and traces of alpha-phellandrene. Product pattern changes markedly to 46% limonene, 9% terpinolene, 23% alpha-pinene, 5% beta-myrcene and 4% a-phellandrene, when Mn2+ is supplied instead of Mg2+
-
?
geranyl diphosphate
terpinolene + diphosphate
-
-
-
-
?
geranyl diphosphate
terpinolene + diphosphate
-
78% (+)-car-3-ene plus 11% terpinolene plus minor products
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?
geranyl diphosphate
terpinolene + diphosphate
-
wild-type produces 49% (+)-car-3-ene, 8.7% (-)-sabinene, 24.7% terpinolene
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?
geranyl diphosphate
terpinolene + diphosphate
-
main product terpinolene, plus minor products (+)-alpha-pinene, gamma-terpinene, alpha-terpinene, (-)-limonene, sabinene, (-)-beta-pinene, and 3-carene
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?
geranyl diphosphate
terpinolene + diphosphate
-
-
products are 28% (-)-alpha-pinene, 35% beta-pinene, 24% camphene, 5% limonene, 2% terpinolene, 6% myrcene, products are 49% (+)-alpha-pinene, 30% camphene, 10% limonene, 5% terpinolene, 6% myrcene
-
?
additional information
?
-
entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate
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-
?
additional information
?
-
-
entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate
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-
?
additional information
?
-
AcTPS1 produces the noncyclic monoterpenes geraniol and beta-myrcene as the major products rather than 1,8-cineole, which is the predominant terpene associated with Actinidia chinensis fruit. Transgenic tobacco leaves expressing AcTPS1 produce beta-myrcene in low amounts as the only gene-specific product. Farnesyl diphosphate is no substrate
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-
?
additional information
?
-
-
AcTPS1 produces the noncyclic monoterpenes geraniol and beta-myrcene as the major products rather than 1,8-cineole, which is the predominant terpene associated with Actinidia chinensis fruit. Transgenic tobacco leaves expressing AcTPS1 produce beta-myrcene in low amounts as the only gene-specific product. Farnesyl diphosphate is no substrate
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-
?
additional information
?
-
the enantiomeric composition of terpenes produced by AaTPS1 in vitro and those produced in ripe Actinidia arguta cv. Hortgem Tahi fruit (stage a3/a4) are very similar
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-
?
additional information
?
-
-
the enantiomeric composition of terpenes produced by AaTPS1 in vitro and those produced in ripe Actinidia arguta cv. Hortgem Tahi fruit (stage a3/a4) are very similar
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-
?
additional information
?
-
the recombinant AaTPS1 enzyme catalyzes the conversion of geranyl diphosphate to both cyclic and noncyclic monoterpene products, kinetics, overview. Specifically, alpha-terpinolene is the predominant terpene produced, accounting for approximately 67% of the total monoterpenes, followed by beta-myrcene (10%), predominantly (S)-limonene (9%), and smaller amounts of alpha-pinene, linalool, and alpha-terpineol. Farnesyl diphosphate is no substrate
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-
?
additional information
?
-
-
the recombinant AaTPS1 enzyme catalyzes the conversion of geranyl diphosphate to both cyclic and noncyclic monoterpene products, kinetics, overview. Specifically, alpha-terpinolene is the predominant terpene produced, accounting for approximately 67% of the total monoterpenes, followed by beta-myrcene (10%), predominantly (S)-limonene (9%), and smaller amounts of alpha-pinene, linalool, and alpha-terpineol. Farnesyl diphosphate is no substrate
-
-
?
additional information
?
-
no substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
no oxygenated or phosphorylated monoterpenes are found in detectable amounts
-
-
?
additional information
?
-
no substrates: farnesyl diphosphate, geranygeranyl diphosphate
-
-
?
additional information
?
-
-
reaction follows a cisoid, anti-endo-pattern. In the case of geranyl diphosphate, a preassociation mechanism is suggested in which optimum folding of the terpenyl chain precedes the initial ionization step. The alternate substratse are ionized by the cyclases prior to their achieving the optimum orientation for bicyclization
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-
?
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malfunction
transcription factors AaNAC2, AaNAC3, and AaNAC4 bind a 28-bp fragment of the proximal NAC binding site in the Actinidia arguta TPS1 promoter but not the Actinidia chinensis AcTPS1 promoter, where the NAC binding site is mutated. Activation can be restored by reintroducing multiple repeats of the 12-bp NAC core-binding motif. The absence of NAC transcriptional activation in ripe Actinidia chinensis fruit can account for the low accumulation of AcTPS1 transcript, protein, and monoterpene volatiles in this species
evolution
Actinidia arguta AaTPS1 and Actinidia chinensis AcTPS1 likely originate from a common ancestral gene, phylogenetic analysis of the AaTPS1 and AcTPS1
evolution
Actinidia chinensis terpene synthase1 (AcTPS1) is identified as part of an array of eight tandemly duplicated genes. Actinidia arguta AaTPS1 and Actinidia chinensis AcTPS1 likely originate from a common ancestral gene, phylogenetic analysis of the AaTPS1 and AcTPS1
evolution
-
transcriptome analysis of the 3 cardinal terpene chemotypes of Melaleuca alternifolia in young leaves, mature leaves, and stem and compared transcript abundance to variation in the constitutive profile of terpenes. The three cardinal chemotypes are dominated by terpinen-4-ol, terpinolene or 1,8-cineole and their biosynthetically related compounds. Chemotype 2 plants (dominated by terpinolene) show a greater degree of differential gene expression compared to the other chemotypes, which might be related to the isolation of plant populations that exhibit this chemotype and the possibility that the terpinolene synthase gene in Melaleuca alternifolia is derived by introgression from a closely related species, Melaleuca trichostachya, multivariate analyses, overview
physiological function
high rates of terpinolene production in ripe Actinidia arguta fruit are correlated with increasing gene and protein expression of Actinidia arguta terpene synthase1 (AaTPS1) and correlates with an increase in transcript levels of the 2-C-methyl-D-erythritol 4-phosphate pathway enzyme 1-deoxy-D-xylulose-5-phosphate synthase (DXS). DXS is likely to be the key step in regulating 2-C-methyl-D-erythritol 4-phosphate substrate flux in kiwifruit. Transcription factors AaNAC2, AaNAC3, and AaNAC4 bind a 28-bp fragment of the proximal NAC binding site in the AaTPS1 promoter but not the Actinidia chinensis AcTPS1 promoter, where the NAC binding site is mutated. Importance of NAC transcription factors in controlling monoterpene production and other traits in ripening fruits. Ripe fruits of Actinidia arguta have a very high amount of terpene volatiles released as compared to other Actinidia species fruits, overview
physiological function
high rates of terpinolene production in ripe Actinidia arguta fruit are correlated with increasing gene and protein expression of Actinidia arguta terpene synthase1 (AaTPS1) and correlates with an increase in transcript levels of the 2-C-methyl-D-erythritol 4-phosphate pathway enzyme 1-deoxy-D-xylulose-5-phosphate synthase (DXS). Importance of NAC transcription factors in controlling monoterpene production and other traits in ripening fruits
physiological function
-
quantitative terpene variation is highly influenced by the combined expression of genes in the methylerythritol 4-phosphate (MEP) pathway, all tissues from chemotype 2 plants contain more terpinolene and 1,8-cineole, very low contents in chemotype 1, and no terpinolene in chemotype 3, determination of total terpene concentration for the three cardinal chemotypes in Melaleuca alternifolia, overview. Emissions from the plants are dominated by the following compounds: chemotype 1 by p-cymene and gamma-terpinene with terpinene-4-ol being the third most abundant compound, chemotype 2 by p-cymene, terpinolene, alpha-pinene, limonene and 1,8-cineole, and chemotype 5 by 1,8-cineole, alpha-pinene and limonene
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A595G
shift in product profile, mutant produces 2.4% (+)-car-3-ene, 39% (-)-sabinene, 33.3% terpinolene
A595G/F596L/L599F
shift in product profile, mutant produces 42.3% (+)-car-3-ene, 7.3% (-)-sabinene, 20.1% terpinolene
F596E
shift in product profile, mutant produces 0.5% (+)-car-3-ene, 10.2% (-)-sabinene, 5.7% terpinolene, 70.9% limonene
F596G
shift in product profile, mutant produces 10.0% (+)-car-3-ene, 11.2% (-)-sabinene, 17.3% terpinolene, 27.0% myrcene, 17.0% limonene
F596H
shift in product profile, mutant produces 2.1% (+)-car-3-ene, 46.5% (-)-sabinene, 27.1% terpinolene
F596L
shift in product profile, mutant produces 28.6% (+)-car-3-ene, 42.8% (-)-sabinene, 36.4% terpinolene
L599F
shift in product profile, mutant produces 1.5% (+)-car-3-ene, 20.2% (-)-sabinene, 32.2% terpinolene
S589A
shift in product profile, mutant produces 1.2% (+)-car-3-ene, 42.9% (-)-sabinene, 35.5% terpinolene
G595A/L596F/F599L
shift in product profile, mutant produces 1.8% (+)-car-3-ene, 23.3% (-)-sabinene, 55.2% terpinolene
G595A/L596F/F599L
shift in product profile, mutant produces 4.7% (+)-car-3-ene, 47.4% (-)-sabinene, 35.2% terpinolene
G595A/L596F/F599L
shift in product profile, mutant produces 5.4% (+)-car-3-ene, 29.0% (-)-sabinene, 26.4% terpinolene
L596F
shift in product profile, mutant produces 12.3% (+)-car-3-ene, 37.4% (-)-sabinene, 35.4% terpinolene
L596F
shift in product profile, mutant produces 5% (+)-car-3-ene, 20.9% (-)-sabinene, 53.5% terpinolene
L596F
shift in product profile, mutant produces 9.2% (+)-car-3-ene, 20.2% (-)-sabinene, 32.2% terpinolene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by (+)-3-carene in (+)-3-carene synthase isoforms. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by or (-)-sabinene. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by or (-)-sabinene. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by or (-)-sabinene. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
additional information
construction of a series of domain swaps and site-directed substitutions between (-)-sabinene synthase and (+)-3-carene synthase isoforms to explore which regions and specific amino acids of these enzymes affect the differences of their product profiles. The amino acid in position 596 is critical for product profiles dominated by or (-)-sabinene. A leucine in this position promotes formation of (+)-3-carene, whereas phenylalanine promotes (-)-sabinene
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Croteau, R.; Satterwhite, D.M.
Biosynthesis of monoterpenes: Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage
J. Biol. Chem.
264
15309-15315
1989
Salvia officinalis
brenda
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Cloning and functional characterization of three terpene synthases from lavender (Lavandula angustifolia)
Arch. Biochem. Biophys.
465
417-429
2007
Lavandula angustifolia (Q2XSC6)
brenda
Huber, D.P.; Philippe, R.N.; Godard, K.A.; Sturrock, R.N.; Bohlmann, J.
Characterization of four terpene synthase cDNAs from methyl jasmonate-induced Douglas-fir, Pseudotsuga menziesii
Phytochemistry
66
1427-1439
2005
Pseudotsuga menziesii (Q4QSN6)
brenda
Bohlmann, J.; Phillips, M.; Ramachandiran, V.; Katoh, S.; Croteau, R.
cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis)
Arch. Biochem. Biophys.
368
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1999
Abies grandis (Q9M7D0), Abies grandis
brenda
Keszei, A.; Hassan, Y.; Foley, W.J.
A Biochemical Interpretation of Terpene Chemotypes in Melaleuca alternifolia
J. Chem. Ecol.
36
652-661
2010
Melaleuca alternifolia
brenda
De Alwis, R.; Fujita, K.; Ashitani, T.; Kuroda, K.
Volatile and non-volatile monoterpenes produced by elicitor-stimulated Cupressus lusitanica cultured cells
J. Plant Physiol.
166
720-728
2009
Hesperocyparis lusitanica
brenda
Fldt, J.; Martin, D.; Miller, B.; Rawat, S.; Bohlmann, J.
Traumatic resin defense in Norway spruce (Picea abies): methyl jasmonate-induced terpene synthase gene expression, and cDNA cloning and functional characterization of (+)-3-carene synthase
Plant Mol. Biol.
51
119-133
2003
Picea abies (Q84SM8)
brenda
Roach, C.R.; Hall, D.E.; Zerbe, P.; Bohlmann, J.
Plasticity and evolution of (+)-3-carene synthase and (-)-sabinene synthase functions of a Sitka spruce monoterpene synthase gene family associated with weevil resistance
J. Biol. Chem.
289
23859-23869
2014
Picea sitchensis (F1CKI6), Picea sitchensis (F1CKI8), Picea sitchensis (F1CKI9), Picea sitchensis (F1CKJ1)
brenda
Bustos-Segura, C.; Padovan, A.; Kainer, D.; Foley, W.J.; Kuelheim, C.
Transcriptome analysis of terpene chemotypes of Melaleuca alternifolia across different tissues
Plant Cell Environ.
40
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Melaleuca alternifolia
brenda
Nieuwenhuizen, N.J.; Chen, X.; Wang, M.Y.; Matich, A.J.; Perez, R.L.; Allan, A.C.; Green, S.A.; Atkinson, R.G.
Natural variation in monoterpene synthesis in kiwifruit transcriptional regulation of terpene synthases by NAC and ethylene-insensitive3-like transcription factors
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167
1243-1258
2015
Actinidia arguta (A0A075EAR1), Actinidia arguta, Actinidia chinensis (A0A075EB43), Actinidia chinensis
brenda