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Information on EC 4.2.3.133 - alpha-copaene synthase
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4.2.3.133 alpha-copaene synthaseIUBMB Comments
Isolated from Helianthus annuus (sunflower). The enzyme also produces beta-caryophyllene, delta-cadinene and traces of other sesquiterpenoids. See EC 4.2.3.13 (+)-delta-cadinene synthase, EC 4.2.3.57 (-)-beta-caryophyllene synthase.
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The enzyme appears in viruses and cellular organisms
Synonyms
(Z)-beta-cubebene/alpha-copaene synthase, alpha-copaene synthase, bifunctional sesquiterpene synthase 1, CsSesquiTPS1, SES1, sesquiterpene synthase, sesquiterpene synthase 1, SeTPS1, TPS04, TPS1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
TPS1
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (-)-alpha-copaene + diphosphate
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, alpha-copaene-forming)
Isolated from Helianthus annuus (sunflower). The enzyme also produces beta-caryophyllene, delta-cadinene and traces of other sesquiterpenoids. See EC 4.2.3.13 (+)-delta-cadinene synthase, EC 4.2.3.57 (-)-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
(+)-delta-cadinene + diphosphate
-
yield of 40% (+)-delta-cadinene
-
?
(2E,6E)-farnesyl diphosphate
alpha-copaene + diphosphate
-
delta-cadinene is one of the two main products, while alpha-muuorlene, beta-caryophyllene, alpha-humulene and alpha-copaene are minor products
-
?
2 (2E,6E)-farnesyl diphosphate
(-)-alpha-copaene + delta-cadinene + 2 diphosphate
-
-
-
-
?
2 (2E,6E)-farnesyl diphosphate
alpha-copaene + delta-cadinene + 2 diphosphate
-
bifunctional sesquiterpene synthase producing both alpha-copaene and delta-cadinene
-
?
geranylgeranyl diphosphate + H2O
(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate
J9PDV7
it is proposed that a basic amino acid residue of the enzyme abstracts a proton from a molecule of water as the hydroxyl adds to the double bond at carbon7 of geranylgeranyl diphosphate. Concerted cyclization occurs and the double bond at carbon14 of geranylgeranyl diphosphate (carbon-3 of (8R)-hydroxy-copalyl diphosphate) is protonated. This concerted mechanism accounts for the addition of a single atom of 18O and a single atom of deuterium to geranylgeranyl diphosphate to form (8R)-hydroxy-copalyl diphosphate
first step in synthesis of sclareol
-
?
(2E,6E)-farnesyl diphosphate
(-)-alpha-copaene + diphosphate
-
yield of 60% (-)-alpha-copaene, products are about 60% (-)-alpha-copaene, 40% (+)-delta-cadinene
-
?
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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
2 (2E,6E)-farnesyl diphosphate
(-)-alpha-copaene + delta-cadinene + 2 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
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
i.e. Citrus aurantium var. sinensis, pineapple sweet orange
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
in orange tissues, the sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total, overview. Small amounts of beta-caryophyllene are detected in all samples, while alpha-copaene, beta-elemene, alpha-humulene, and alpha-selinene are emitted by all tissues except young leaves. Beside this, each tissue shows a characteristic sesquiterpene emission profile. Major sesquiterpenes emitted by adult leaves are beta-elemene and beta-caryophyllene, while flowers emitt nerolidol, absent from most tissues analyzed. In fruit tissues, valencene emission contributes greatly to total emitted volatiles, in much more extent in peel than in pulp
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
-
tuber-specific over-expression of potato alpha-copaene synthase gene results in up to 15fold enhanced levels of alpha-copaene with a positive correlation between transgene expression level and alpha-copaene abundance. No aroma differences in the transgenic samples compared with controls and no significant differences in taste attributes are found. Sensory analysis suggests that alpha-copaene is not a major component of potato flavour
physiological function
in sweet orange tissues sesquiterpene profile is qualitatively rich. Overall, up to 25 sesquiterpenes are identified in total. Enzyme CsSesquiTPS1 catalyzes formation of a 62:38% mixture of (Z)-beta-cubebene and alpha-copaene
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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). CS_HELAN
555
0
64263
Swiss-Prot
other Location (Reliability: 4)
STS1_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
338
0
38401
Swiss-Prot
other Location (Reliability: 3)
TPS1_PHYDL
564
0
65602
Swiss-Prot
Chloroplast (Reliability: 5)
TPS1_RICCO
558
0
64392
Swiss-Prot
Chloroplast (Reliability: 4)
TPS8_MAIZE
539
0
62026
Swiss-Prot
other Location (Reliability: 3)
STS10_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
336
0
38275
Swiss-Prot
other Location (Reliability: 4)
FARS_MAIZE
533
0
61534
Swiss-Prot
other Location (Reliability: 3)
STS2_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
338
0
38419
Swiss-Prot
other Location (Reliability: 4)
A0A2G9HYY5_9LAMI
181
0
21246
TrEMBL
other Location (Reliability: 2)
A0A2G9HYY6_9LAMI
181
0
21137
TrEMBL
other Location (Reliability: 5)
A0A2G9G8D1_9LAMI
300
0
35271
TrEMBL
other Location (Reliability: 3)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae strain EPY300 as a thioredoxin-fusion protein
gene CsSesquiTPS1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, the enzyme encoded by CsSesquiTPS1 produces a 62:38% mixture of (Z)-beta-cubebene and alpha-copaene
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
nutrition
-
tuber-specific over-expression of potato alpha-copaene synthase gene results in up to 15fold enhanced levels of alpha-copaene with a positive correlation between transgene expression level and alpha-copaene abundance. No aroma differences in the transgenic samples compared with controls and no significant differences in taste attributes are found. Sensory analysis suggests that alpha-copaene is not a major component of potato flavour
synthesis
expression in Saccharomyces cerevisiae leads to a titer of (-)-alpha-copaene of 9 mg/l at 48 h and around 7 mg/l in Escherichia coli, and the titer of (+)-delta-cadinene is 6 mg/l in Saccharomyces cerevisiae and 3.5 mg/l in Escherichia coli
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Goepfert, J.C.; Macnevin, G.; Ro, D.K.; Spring, O.
Identification, functional characterization and developmental regulation of sesquiterpene synthases from sunflower capitate glandular trichomes
BMC Plant Biol.
9
86
2009
Helianthus annuus (Q4U3F6)
brenda
Attia, M.; Kim, S.U.; Ro, D.K.
Molecular cloning and characterization of (+)-epi-alpha-bisabolol synthase, catalyzing the first step in the biosynthesis of the natural sweetener, hernandulcin, in Lippia dulcis
Arch. Biochem. Biophys.
527
37-44
2012
Phyla dulcis (J7LP58)
brenda
Morris, W.L.; Ducreux, L.J.; Shepherd, T.; Lewinsohn, E.; Davidovich-Rikanati, R.; Sitrit, Y.; Taylor, M.A.
Utilisation of the MVA pathway to produce elevated levels of the sesquiterpene alpha-copaene in potato tubers
Phytochemistry
72
2288-2293
2011
Solanum tuberosum
brenda
Xie, X.; Kirby, J.; Keasling, J.D.
Functional characterization of four sesquiterpene synthases from Ricinus communis (castor bean)
Phytochemistry
78
20-28
2012
Ricinus communis (B9S9Z3)
brenda
Guennewich, N.; Higashi, Y.; Feng, X.; Choi, K.B.; Schmidt, J.; Kutchan, T.M.
A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate
Phytochemistry
91
93-99
2013
Salvia sclarea (J9PDV7)
brenda
Alquezar, B.; Rodriguez, A.; de la Pena, M.; Pena, L.
Genomic analysis of terpene synthase family and functional characterization of seven sesquiterpene synthases from Citrus sinensis
Front. Plant Sci.
8
1481
2017
Citrus sinensis (D0UZK2)
brenda
Chuang, L.; Wen, C.H.; Lee, Y.R.; Lin, Y.L.; Hsu, L.R.; Wang, S.Y.; Chu, F.H.
Identification, functional characterization, and seasonal expression patterns of five sesquiterpene synthases in Liquidambar formosana
J. Nat. Prod.
81
1162-1172
2018
Liquidambar formosana
brenda
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