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Information on EC 4.2.3.57 - (-)-beta-caryophyllene synthase
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EC Tree
4.2.3.57 (-)-beta-caryophyllene synthaseIUBMB Comments
Widely distributed in higher plants, cf. EC 4.2.3.89 (+)-beta-caryophyllene synthase.
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Word Map
- 4.2.3.57
-
sesquiterpene
-
terpene
-
e-beta-caryophyllene
-
enemies
- diabrotica
-
herbivore-induced
- virgifera
- biofuel production
- agriculture
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
tps23, tps21, pncps, beta-caryophyllene synthase, at5g23960, okbcs, (e)-beta-caryophyllene synthase, tps04, rttps1, rttps3, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CarS
TPS1
tps23
TPS3
additional information
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (-)-beta-caryophyllene + diphosphate
-
-
-
-
(2E,6E)-farnesyl diphosphate = (-)-beta-caryophyllene + diphosphate
possible mechanism of sesquiterpene synthases from Piper nigrum, the reaction mechanism includes a 1,10-ring closure, overview
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(-)-beta-caryophyllene-forming]
Widely distributed in higher plants, cf. EC 4.2.3.89 (+)-beta-caryophyllene synthase.
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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
(2E,6E)-farnesyl diphosphate
(-)-beta-caryophyllene + alpha-humulene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(E)-beta-caryophyllene + alpha-humulene + alpha-copaene + diphosphate
-
-
alpha-humulene and alpha-copaene are minor products besides the main product (E)-beta-caryophyllene
-
?
(2E,6E)-farnesyl diphosphate
(E)-beta-caryophyllene + alpha-humulene + diphosphate
-
TPS 1 forms two main products: (E)-beta-caryophyllene and alpha-humulene with 76.3 and 23.7%, respectively
-
?
(2E,6E)-farnesyl diphosphate
(E)-beta-caryophyllene + alpha-humulene + germacrene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(trans)-beta-caryophyllene + diphosphate
-
-
-
-
?
Geranyl diphosphate
?
-
production of several monoterpenes among which myrcene, limonene and camphene can be clearly identified
-
?
(2E,6E)-farnesyl diphosphate
(-)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(E)-beta-caryophyllene + diphosphate
-
79% (E)-beta-caryophyllene plus 21% alpha-humulene
-
?
(2E,6E)-farnesyl diphosphate
(E)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
stereochemistry not specified in the publication
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
enzyme produces beta-caryophyllene and alpha-humulene in a ratio of 71:29
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
the enzyme stereochemistry is not determined in the publication. Recombinant enzyme OkBCS converts farnesyl diphosphate to beta-caryophyllene as a major product (94%) and 6% alpha-humulene
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
the enzyme stereochemistry is not determined in the publication
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
the enzyme stereochemistry is not determined in the publication, the reaction mechanism includes a 1,10-ring closure
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
-
-
?
additional information
?
-
enzyme OkBCS is not active with geranyl diphosphate (GPP) as substrate, besides a weak hydrolysis activity converting GPP to geraniol, identification of substrates and products by GC-MS analysis
-
-
?
additional information
?
-
-
enzyme OkBCS is not active with geranyl diphosphate (GPP) as substrate, besides a weak hydrolysis activity converting GPP to geraniol, identification of substrates and products by GC-MS analysis
-
-
?
additional information
?
-
the enzyme encoded by gene TPS1 produces beta-caryophyllene as a main product and humulene as a minor compound, and thus is named caryophyllene synthase (PnCPS)
-
-
?
additional information
?
-
steady-state kinetic parameters are determined using malachite green phosphate assay
-
-
?
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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
(2E,6E)-farnesyl diphosphate
(-)-beta-caryophyllene + alpha-humulene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(E)-beta-caryophyllene + alpha-humulene + germacrene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(trans)-beta-caryophyllene + diphosphate
-
-
-
-
?
additional information
?
-
the enzyme encoded by gene TPS1 produces beta-caryophyllene as a main product and humulene as a minor compound, and thus is named caryophyllene synthase (PnCPS)
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
stereochemistry not specified in the publication
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
the enzyme stereochemistry is not determined in the publication
-
-
?
(2E,6E)-farnesyl diphosphate
beta-caryophyllene + diphosphate
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0211
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
0.0289
(2E,6E)-farnesyl diphosphate
30°C, pH not specified in the publication
0.1255
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
additional information
additional information
steady state kinetics
-
additional information
additional information
-
steady state kinetics
-
additional information
additional information
Michaelis-Menten steady-state kinetics
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.455
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
4.06
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
21.6
(2E,6E)-farnesyl diphosphate
pH not specified in the publication, 30°C, recombinant His-tagged enzyme
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pH OPTIMUM
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
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
unripe peppercorn is subjected to the Illumina transcriptome sequencing, young, unripe, and ripe fruits. GC/MS profiling of terpenes from immature black pepper fruit, accumulation of beta-caryophyllene, the major sesquiterpene in peppercorn, changes from 46% to 70% as fruits ripen
brenda
additional information
highest expression in stage 2 inflorescences, transcript levels are over 30fold higher than those of leaves
brenda
slight expression in young leaf, medium leaf and old leaf
brenda
higher beta-caryophyllene contents in mature leaves compared to young leaves
brenda
additional information
expression variation of OkBCS well corroborate with beta-caryophyllene levels in different tissues from five Ocimum species
brenda
additional information
-
expression variation of OkBCS well corroborate with beta-caryophyllene levels in different tissues from five Ocimum species
brenda
additional information
isozyme expression patterns, overview
brenda
additional information
isozyme expression patterns, overview
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
isozyme RtTPS1 contains no typical N-terminal transit peptide (62-64aa)
brenda
isozyme RtTPS3 contains no typical N-terminal transit peptide (62-64aa)
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
additional information
evolution
isozyme RtTPS1 contains all the conserved domains of the TPS family, including the RR(P)X8W, RXR, and DDXXD (X is any amino acid) motifs, and absolutely conserved arginine, cysteine and histidine residues in active-site
evolution
isozyme RtTPS3 contains all the conserved domains of the TPS family, including the RR(P)X8W, RXR, and DDXXD (X is any amino acid) motifs, and absolutely conserved arginine, cysteine and histidine residues in active-site
evolution
the cyclization process catalyzed by PnTPSs follows a 1,10-closure mechanism assuming that the present PnTPSs have evolved from a common ancestor
evolution
the enzyme belongs to typical class of sesquiterpene synthases from angiosperms, clade TPS-a. Across five Ocimum species, OkBCS shows the highest expression in Ocimum kilimandscharicum followed by Ocimum americanum, Ocimum tenuiflorum, and Ocimum gratissimum while Ocimum basilicum hadve trace levels
metabolism
beta-caryophyllene is produced via the mevalonate (MVA)-mediated pathway, overview
metabolism
beta-caryophyllene is produced via the mevalonate (MVA)-mediated pathway, overview
metabolism
GC/MS profiling of terpenes from immature black pepper fruit, accumulation of beta-caryophyllene, the major sesquiterpene in peppercorn, changes from 46% to 70% as fruits ripen
metabolism
putative alpha-pinene and beta-caryophyllene biosynthesis pathway
physiological function
flowers of plant lines lacking (E)-beta-caryophyllene emission show greater bacterial growth on their stigmas than wild-type flowers, and their seeds are lighter and misshapen. Plant lines with ectopic (E)-beta-caryophyllene emission from vegetative parts are more resistant than wild-type plants to pathogen infection of leaves, and show reduced cell damage and higher seed production. (E)-beta-caryophyllene seems to act by direct inhibition of bacterial growth
physiological function
agro-infiltration based transient expression manipulation with OkBCS overexpression and silencing confirms its role in beta-caryophyllene biosynthesis
additional information
-
isozymes RtTPS1-4 mainly produce (+)-alpha-pinene and (+)-beta-pinene, as well as small amounts of (-)-alpha-pinene and (-)-beta-pinene with GPP, while RtTPS1 and RtTPS3 are also active with FPP, producing beta-caryophyllene (65.71% for RtTPS1 and 93.05% for RtTPS3), along with a smaller amount of alpha-humulene (4.29% for RtTPS1 and 6.95% for RtTPS3). alpha/beta-Pinene, beta-caryophyllene, and alpha-humulene constitute the major active components in Rhodomyrtus tomentosa. Among them, (+)-alpha-pinene and beta-caryophyllene are most abundant in the leaves
additional information
isozymes RtTPS1-4 mainly produce (+)-alpha-pinene and (+)-beta-pinene, as well as small amounts of (-)-alpha-pinene and (-)-beta-pinene with GPP, while RtTPS1 and RtTPS3 are also active with FPP, producing beta-caryophyllene (65.71% for RtTPS1 and 93.05% for RtTPS3), along with a smaller amount of alpha-humulene (4.29% for RtTPS1 and 6.95% for RtTPS3). alpha/beta-Pinene, beta-caryophyllene, and alpha-humulene constitute the major active components in Rhodomyrtus tomentosa. Among them, (+)-alpha-pinene and beta-caryophyllene are most abundant in the leaves
additional information
isozymes RtTPS1-4 mainly produce (+)-alpha-pinene and (+)-beta-pinene, as well as small amounts of (-)-alpha-pinene and (-)-beta-pinene with GPP, while RtTPS1 and RtTPS3 are also active with FPP, producing beta-caryophyllene (65.71% for RtTPS1 and 93.05% for RtTPS3), along with a smaller amount of alpha-humulene (4.29% for RtTPS1 and 6.95% for RtTPS3). alpha/beta-Pinene, beta-caryophyllene, and alpha-humulene constitute the major active components in Rhodomyrtus tomentosa. Among them, (+)-alpha-pinene and beta-caryophyllene are most abundant in the leaves
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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). BCAS_SACES
Saccharothrix espanaensis (strain ATCC 51144 / DSM 44229 / JCM 9112 / NBRC 15066 / NRRL 15764)
353
0
39205
Swiss-Prot
-
TPS4_PHYPO
337
0
38751
Swiss-Prot
other Location (Reliability: 4)
TATC6_HYPAT
386
0
44939
Swiss-Prot
Mitochondrion (Reliability: 3)
FARS_MAIZE
533
0
61534
Swiss-Prot
other Location (Reliability: 3)
TPS8_MAIZE
539
0
62026
Swiss-Prot
other Location (Reliability: 3)
BCPSD_ORIVU
554
0
64724
Swiss-Prot
other Location (Reliability: 4)
BCPSF_ORIVU
554
0
64662
Swiss-Prot
other Location (Reliability: 4)
TPS1_MATCR
547
0
63465
Swiss-Prot
other Location (Reliability: 2)
TPS1_PHYPO
334
0
38880
Swiss-Prot
other Location (Reliability: 3)
TPS1_PIPNI
559
0
64936
Swiss-Prot
Secretory Pathway (Reliability: 5)
TS23B_MAIZE
547
0
63658
Swiss-Prot
other Location (Reliability: 2)
TS23M_MAIZE
547
0
63483
Swiss-Prot
other Location (Reliability: 2)
CARS_ARTAN
548
0
63737
Swiss-Prot
other Location (Reliability: 3)
CARS_LAVAN
548
0
63644
Swiss-Prot
other Location (Reliability: 2)
CARS_TANPA
548
0
63519
Swiss-Prot
other Location (Reliability: 3)
TPS12_SOLHA
545
0
63985
Swiss-Prot
other Location (Reliability: 3)
TPS12_SOLLC
548
0
64321
Swiss-Prot
other Location (Reliability: 5)
TPS1_XANST
548
0
64501
Swiss-Prot
other Location (Reliability: 2)
A0A2D1CN32_MENAQ
85
0
10084
TrEMBL
other Location (Reliability: 5)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
production of beta-caryophyllene by assembling a biosynthetic pathway in an engineered Escherichia coli strain of which phosphoglucose isomerase gene has been deleted. The 1-deoxy-D-xylulose 5-phosphate (DXP) or heterologous mevalonate (MVA) pathways are employed. Geranyl diphosphate synthase (GPPS2 gene from Abies grandis), glucose-6-phosphate dehydrogenase (G6PDH gene), and beta-caryophyllene synthase genes are co-overexpressed in the engineered strain. The final genetically modified strain, YJM59, produces 220 mg/l of beta-caryophyllene in flask culture. Evaluation of fed-batch fermentation for the production of beta-caryophyllene. After induction for 60 h, the YJM59 strain produces beta-caryophyllene at a concentration of 1520 mg/l. The volumetric production fermented in the aerobic fed-batch is 0.34 mg/(l/h/OD600) and the conversion efficiency of glucose to beta-caryophyllene (gram to gram) is 1.69%. Method evaluation with beta-caryophyllene synthases from different origins, QHS1 from Artemisia annua is the most effective of the three enzymes, compared to TPS21 from Arabidopsis thaliana and TPS23 from Zea perennis. Substrate channeling
additional information
in a robustly acetate-utilizing Escherichia coli strain, acetyl-CoA synthase (ACS), Artemisia annua beta-caryophyllene synthase (QHS1) and geranyl diphosphate synthase (GPPS2) are co-expressed to establish the engineered strain converting acetic acid to beta-caryophyllene. To further enhance beta-caryophyllene production from acetic acid, the heterologous mevalonate pathway is introduced into the cells. Acetoacetyl-CoA synthase (AACS) is also expressed in the cells to increase the precursor acetoacetyl-CoA and accordingly resulted in the increase of beta-caryophyllene. The final genetically modified strain, YJM67, accumulates the production of biomass and beta-caryophyllene up to 12.6 and 1.05 g/l during 72 h, respectively, with a specific productivity of 1.15 mg/h/g dry cells, and the conversion efficiency of acetic acid to beta-caryophyllene (gram to gram) reaching 2.1%. The yield of beta-caryophyllene on acetic acid of this strain also reaches about 5.6 % of the theoretical yield. A pH-coupled HAc fed-batch fermentation in large scale production of beta-caryophyllene
additional information
production of beta-caryophyllene by assembling a biosynthetic pathway in an engineered Escherichia coli strain of which phosphoglucose isomerase gene has been deleted. The 1-deoxy-D-xylulose 5-phosphate (DXP) or heterologous mevalonate (MVA) pathways are employed. Geranyl diphosphate synthase (GPPS2 gene from Abies grandis), glucose-6-phosphate dehydrogenase (G6PDH gene), and beta-caryophyllene synthase genes are co-overexpressed in the engineered strain. The final genetically modified strain, YJM59, produces 220 mg/l of beta-caryophyllene in flask culture. Evaluation of fed-batch fermentation for the production of beta-caryophyllene. After induction for 60 h, the YJM59 strain produces beta-caryophyllene at a concentration of 1520 mg/l. The volumetric production fermented in the aerobic fed-batch is 0.34 mg/(l/h/OD600) and the conversion efficiency of glucose to beta-caryophyllene (gram to gram) is 1.69%. Method evaluation with beta-caryophyllene synthases from different origins, QHS1 from Artemisia annua is the most effective of the three enzymes, compared to TPS21 from Arabidopsis thaliana and TPS23 from Zea perennis. Substrate channeling
additional information
gene OkBCS silencing in Ocimum kilimandscharicum plants via Agrobacterium tumefaciens strain GV3101 mediated transfection. beta-Caryophyllene and alpha-humulene levels decrease by about 20% in silenced plants compared to controls. The silencing effect is more prominent in systemic leaves with 95% reduction in OkBCS transcripts against 51% decrease in local leaves
additional information
-
gene OkBCS silencing in Ocimum kilimandscharicum plants via Agrobacterium tumefaciens strain GV3101 mediated transfection. beta-Caryophyllene and alpha-humulene levels decrease by about 20% in silenced plants compared to controls. The silencing effect is more prominent in systemic leaves with 95% reduction in OkBCS transcripts against 51% decrease in local leaves
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant C-terminally His6-tagged enzyme from Escherichia coli TOP10 cells by nickel affinity chromatography to homogeneity
recombinant His-tagged enzyme TPS1 from Escherichia coli strain Rosetta 2(DE3) by nickel affinity chromatography, desalting gel filtration, and ultrafiltration
recombinant His-tagged isozyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
codon-optimized QHS1 gene, recombinant overexpression in Escherichia coli strain YJM59, coexpression with geranyl diphosphate synthase (GPPS2 gene from Abies grandis), glucose-6-phosphate dehydrogenase (G6PDH gene) from plasmid pACY-mvaE-mvaS-QHS1-GPPS2-G6PDH
expressed in Escherichia coli BL21, Rosetta and RIPL strains and in Arabidopsis thaliana
expressed in Escherichia coli strain YJM59
gene OkBCS, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, quantitative RT-PCR expression analysis, recombinant expression of C-terminally His6-tagged enzyme in Escherichia coli TOP10 cells, transient overexpression in Ocimum kilimandscharicum via Agrobacterium tumefaciens strain GV3101 mediated transfection
gene QHS1, the optimized QHS1 gene is expressed in Escherichia coli strain YJM63 and BL21(DE3), coexpression with genes ACS, GPPS2, and AACS to construct a beta-caryophyllene overroduction strain
gene TPS1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis and tree, the enzyme encoded by gene TPS1 produces beta-caryophyllene as a main product and humulene as a minor compound, and thus is named caryophyllene synthase (PnCPS), illumina transcriptome sequencing of unripe peppercorn identifiying sesquiterpene synthases (sesqui-TPSs), recombinant expression of His-tagged enzyme TPS1 in Escherichia coli strain Rosetta 2(DE3)
gene TPS1, sequence comparisons and phylogenetic tree, isozyme TPS1 RT-PCR expression analysis, recombinant expression of His-tagged isozyme in Escherichia coli strain BL21(DE3)
gene TPS21, recombinant overexpression in Escherichia coli strain YJM59, coexpression with geranyl diphosphate synthase (GPPS2 gene from Abies grandis), glucose-6-phosphate dehydrogenase (G6PDH gene) from plasmid pACY-mvaE-mvaS-QHS1-GPPS2-G6PDH
gene TPS3, sequence comparisons and phylogenetic tree, isozyme TPS3 RT-PCR expression analysis, recombinant expression of His-tagged isozyme in Escherichia coli strain BL21(DE3)
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme expression is enhanced in Pseudomonas protegens CHA0-colonized maize roots after 72 h of Diabrotica balteata feeding
-
Methyl jasmonate treatment results in a significant increase of TPS1 transcript accumulation in all developmental stages of the leaves
transcript level of TPS 1 is significantly higher in oviposition-induced twigs that are attractive to the parasitoid Diprion pini than in non-attractive, artificially damaged twigs. Transcript levels of PsTPS 1 also changes significantly over time