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Information on EC 4.2.3.73 - valencene synthase
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EC Tree
4.2.3.73 valencene synthaseIUBMB Comments
The recombinant enzyme from Vitis vinifera gave 49.5% (+)-valencene and 35.5% (-)-7-epi-alpha-selinene. Initial cyclization gives (+)-germacrene A in an enzyme bound form which is not released to the medium.
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Word Map
- 4.2.3.73
-
sesquiterpene
-
+-valencene
- citrus
-
flavor
-
terpenoids
- nootkatensis
- aroma
- synthesis
- mevalonate
-
+-nootkatone
- sesquiterpenoids
-
carotenoid
- grapefruit
- cypress
- squalene
-
heartwood
- muticus
-
hyoscyamus
-
mandarin
- vinifera
-
murcott
-
alaska
- n-dodecane
-
grapevine
-
fragrance
- germacrene
The enzyme appears in viruses and cellular organisms
Synonyms
valencene synthase, vvval, (+)-valencene synthase, valcs, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(+)-valencene synthase
terpene synthase 1
TPS1
ValCS
VvVal
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (+)-valencene + diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (valencene-forming)
The recombinant enzyme from Vitis vinifera gave 49.5% (+)-valencene and 35.5% (-)-7-epi-alpha-selinene. Initial cyclization gives (+)-germacrene A in an enzyme bound form which is not released to the medium.
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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
(+)-valencene + beta-elemene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-valencene + diphosphate
-
plus minor product germacrene A. At pH 7, germacrene A accounts for approximately 6% of the total sesquiterpenes produced. With increasing pH, the amount of side-product germacrene A also increases
-
?
(2E,6E)-farnesyl diphosphate
(+)-valencene + diphosphate
Q71MJ3
-
single product
-
?
(2E,6E)-farnesyl diphosphate
(+)-valencene + diphosphate
-
49.5% (+)-valencene and 35.5% (-)-7-epi-alpha-selinene, plus minor amounts of alpha-selinene, epi-aristolochene, E-beta-caryophyllene, alpha-humulene
-
?
(2E,6E)-farnesyl diphosphate
(+)-valencene + diphosphate
-
about 49%, plus 35.5% (-)-7-epi-alpha-selinene
-
?
(2E,6E)-farnesyl diphosphate
(+)-valencene + diphosphate
-
-
49.5% (+)-valencene and 35.5% (-)-7-epi-alpha-selinene, plus minor amounts of alpha-selinene, epi-aristolochene, E-beta-caryophyllene, alpha-humulene
-
?
farnesyl diphosphate
(+)-valencene + diphosphate
-
49.5% (+)-valencene and 35.5% (-)-7-epi-alpha-selinene, plus minor amounts of alpha-selinene, epi-aristolochene, E-beta-caryophyllene, alpha-humulene
-
?
farnesyl diphosphate
(+)-valencene + diphosphate
-
plus 7-epi-alpha-selinene
-
?
farnesyl diphosphate
(+)-valencene + diphosphate
-
-
49.5% (+)-valencene and 35.5% (-)-7-epi-alpha-selinene, plus minor amounts of alpha-selinene, epi-aristolochene, E-beta-caryophyllene, alpha-humulene
-
?
farnesyl diphosphate
(+)-valencene + diphosphate
-
plus 7-epi-alpha-selinene
-
?
additional information
?
-
-
no substrate: geranyl diphosphate or geranylgeranyl diphosphate
-
-
?
additional information
?
-
no substrate: geranyl diphosphate or geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
no substrate: geranyl diphosphate or geranylgeranyl diphosphate
-
-
?
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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
(+)-valencene + beta-elemene + diphosphate
-
-
-
?
farnesyl diphosphate
(+)-valencene + diphosphate
-
49.5% (+)-valencene and 35.5% (-)-7-epi-alpha-selinene, plus minor amounts of alpha-selinene, epi-aristolochene, E-beta-caryophyllene, alpha-humulene
-
?
farnesyl diphosphate
(+)-valencene + diphosphate
-
-
49.5% (+)-valencene and 35.5% (-)-7-epi-alpha-selinene, plus minor amounts of alpha-selinene, epi-aristolochene, E-beta-caryophyllene, alpha-humulene
-
?
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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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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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
additional information
male flower parts of grapevines are responsible for sesquiterpenoid floral scent formation. Sesquiterpene volatiles, which are emitted with a light-dependent diurnal pattern early in the morning at prebloom and bloom, are localized to anthers and, more specifically, within the developing pollen grains
brenda
strongest hybridization signals with RNA from flower budsand strongly reduced transcript levels in pre- and postanthesis open flowers and in set flowers at early fruit onset
brenda
-
male flower parts of grapevines are responsible for sesquiterpenoid floral scent formation. Sesquiterpene volatiles, which are emitted with a light-dependent diurnal pattern early in the morning at prebloom and bloom, are localized to anthers and, more specifically, within the developing pollen grains
-
brenda
transcripts become detectable in September, almost two months after flowering, then increase and reach a maximum at the final sample date in early October when the fruit is at peak maturity
brenda
detection of VvVal transcripts coincides with the stabilization of acid levels in the fruits following a four-week period of rapid depletion
brenda
-
transcripts become detectable in September, almost two months after flowering, then increase and reach a maximum at the final sample date in early October when the fruit is at peak maturity
-
brenda
additional information
expression in different tissues from the tree correlates well with nootkatone content
brenda
additional information
-
expression in different tissues from the tree correlates well with nootkatone content
brenda
additional information
-
transcript levels are low in open pre-anthesis flowers, flowers after anthesis, or at early onset of fruit development
brenda
additional information
transcript levels are low in open pre-anthesis flowers, flowers after anthesis, or at early onset of fruit development
brenda
additional information
-
transcript levels are low in open pre-anthesis flowers, flowers after anthesis, or at early onset of fruit development
-
brenda
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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). TPS1_CITSI
548
0
63677
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)
TPSVS_VITVI
556
0
64432
Swiss-Prot
other Location (Reliability: 5)
A0A649UKC0_CITLI
118
0
14006
TrEMBL
other Location (Reliability: 3)
A0A2I0AH28_9ASPA
108
0
12494
TrEMBL
other Location (Reliability: 2)
A0A2I0AH40_9ASPA
500
0
58891
TrEMBL
Secretory Pathway (Reliability: 5)
A0A2I0ABC5_9ASPA
563
0
65245
TrEMBL
other Location (Reliability: 5)
A0A649UJ29_CITLI
119
0
14361
TrEMBL
other Location (Reliability: 2)
A0A2H9ZZW7_9ASPA
133
0
15370
TrEMBL
other Location (Reliability: 3)
A0A649UK17_CITLI
118
0
13774
TrEMBL
other Location (Reliability: 2)
A0A2I0ABI5_9ASPA
507
0
59528
TrEMBL
other Location (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is developmentally regulated, transcript accumulates only towards fruit maturation. Expression is responsive to ethylene
Q71MJ3
transcript levels are low in open pre-anthesis flowers, flowers after anthesis, or at early onset of fruit development
transcript levels are low in open pre-anthesis flowers, flowers after anthesis, or at early onset of fruit development
transcript levels are low in open pre-anthesis flowers, flowers after anthesis, or at early onset of fruit development
-
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
Q71MJ3
8fold improvement in the production of valencene, in yeast co-engineered with a truncated and deregulated HMG1, mitochondrion-targeted heterologous farnesyl diphosphate synthase and a mitochondrion-targeted sesquiterpene synthase,i.e.valencene synthase. Production of the Citrus sesquiterpene valencene in yeast is affected by deletion of geranylgeranyl diphosphate synthase BTS1 but not of phosphatases DPP1 or LPP1
synthesis
expression of valencene synthase in Saccharomyces cerevisiae indicates potential for higher yields. In an optimized Rhodobacter sphaeroides strain, expression of valencene synthase increases valencene yields 14fold to 352 mg/l
synthesis
Q71MJ3
heterologous expression of the (+)-valencene synthase gene in Corynebacterium glutamicum is not sufficient to enable (+)-valencene production, likely because provision of farnesyl diphosphate by endogenous prenyltransferases is too low. Upon deletion of two endogenous prenyltransferase genes and heterologous expression of either farnesyl diphosphate synthase gene ispA from Escherichia coli or ERG20 from Saccharomyces cerevisiae (+)-valencene production is observed. n-Dodecane is suitable for extraction of (+)-valencene from cultures and compatible with growth of Corynabacterium glutamicum. Production based on (+)-valencene synthase from Nootka cypress is superior to production by the enzyme from Citrus sinensis
synthesis
heterologous expression of the (+)-valencene synthase gene in Corynebacterium glutamicum is not sufficient to enable (+)-valencene production, likely because provision of farnesyl diphosphate by endogenous prenyltransferases is too low. Upon deletion of two endogenous prenyltransferase genes and heterologous expression of either farnesyl diphosphate synthase gene ispA from Escherichia coli or ERG20 from Saccharomyces cerevisiae (+)-valencene production is observed. n-Dodecane is suitable for extraction of (+)-valencene from cultures and compatible with growth of Corynabacterium glutamicum. Production based on (+)-valencene synthase from Nootka cypress is superior to production by the enzyme from Citrus sinensis
synthesis
Introduction of a valencene synthase gene into mushroom-forming fungus Schizophyllum commune results in production of the sesquiterpene (+)-valencene, both in mycelium and in fruiting bodies. Levels of (+)-valencene in culture media of strains containing a mutated RGS regulatory protein gene are increased fourfold compared to those in wild-type transformants. Up to 16 mg l/1 (+)-valencene can be produced. The amount of (+)-valencene containing n-dodecane recovered from the culture medium increases six- to sevenfold in the mutant strains due to the absence of schizophyllan
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Luecker, J.; Bowen, P.; Bohlmann, J.
Vitis vinifera terpenoid cyclases: functional identification of two sesquiterpene synthase cDNAs encoding (+)-valencene synthase and (-)-germacrene D synthase and expression of mono- and sesquiterpene synthases in grapevine flowers and berries
Phytochemistry
65
2649-2659
2004
Vitis vinifera, Vitis vinifera (Q6Q3H2), Vitis vinifera cv. Gewuerztraminer
brenda
Farhi, M.; Marhevka, E.; Masci, T.; Marcos, E.; Eyal, Y.; Ovadis, M.; Abeliovich, H.; Vainstein, A.
Harnessing yeast subcellular compartments for the production of plant terpenoids
Metab. Eng.
13
474-481
2011
Citrus sinensis (Q71MJ3)
brenda
Sharon-Asa, L.; Shalit, M.; Frydman, A.; Bar, E.; Holland, D.; Or, E.; Lavi, U.; Lewinsohn, E.; Eyal, Y.
Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene
Plant J.
36
664-674
2003
Citrus sinensis (Q71MJ3)
brenda
Martin, D.M.; Toub, O.; Chiang, A.; Lo, B.C.; Ohse, S.; Lund, S.T.; Bohlmann, J.
The bouquet of grapevine (Vitis vinifera L. cv. Cabernet Sauvignon) flowers arises from the biosynthesis of sesquiterpene volatiles in pollen grains
Proc. Natl. Acad. Sci. USA
106
7245-7250
2009
Vitis vinifera (Q6Q3H2), Vitis vinifera L. cv. Cabernet Sauvignon (Q6Q3H2)
brenda
Scholtmeijer, K.; Cankar, K.; Beekwilder, J.; Woesten, H.A.; Lugones, L.G.; Bosch, D.
Production of (+)-valencene in the mushroom-forming fungus S. commune
Appl. Microbiol. Biotechnol.
98
5059-5068
2014
Callitropsis nootkatensis (V9N2L5)
brenda
Frohwitter, J.; Heider, S.; Peters-Wendisch, P.; Beekwilder, J.; Wendisch, V.
Production of the sesquiterpene (+)-valencene by metabolically engineered Corynebacterium glutamicum
J. Biotechnol.
191
205-213
2014
Citrus sinensis (Q71MJ3), Citrus sinensis, Callitropsis nootkatensis (V9N2L5), Callitropsis nootkatensis
brenda
Beekwilder, J.; van Houwelingen, A.; Cankar, K.; van Dijk, A.D.; de Jong, R.M.; Stoopen, G.; Bouwmeester, H.; Achkar, J.; Sonke, T.; Bosch, D.
Valencene synthase from the heartwood of Nootka cypress (Callitropsis nootkatensis) for biotechnological production of valencene
Plant Biotechnol. J.
12
174-182
2014
Callitropsis nootkatensis (V9N2L5), Callitropsis nootkatensis
brenda
Guo, X.; Sun, J.; Li, D.; Lu, W.
Heterologous biosynthesis of (+)-nootkatone in unconventional yeast Yarrowia lipolytica
Biochem. Eng. J.
137
125-131
2018
Callitropsis nootkatensis
-
brenda
Cankar, K.; Jongedijk, E.; Klompmaker, M.; Majdic, T.; Mumm, R.; Bouwmeester, H.; Bosch, D.; Beekwilder, J.
(+)-Valencene production in Nicotiana benthamiana is increased by down-regulation of competing pathways
Biotechnol. J.
10
180-189
2015
Callitropsis nootkatensis (S4SC87)
brenda
Yu, Q.; Plotto, A.; Baldwin, E.; Bai, J.; Huang, M.; Yu, Y.; Dhaliwal, H.; Gmitter, F.J.
Proteomic and metabolomic analyses provide insight into production of volatile and non-volatile flavor components in mandarin hybrid fruit
BMC Plant Biol.
15
76
2015
Citrus reticulata
brenda
Shen, S.L.; Yin, X.R.; Zhang, B.; Xie, X.L.; Jiang, Q.; Grierson, D.; Chen, K.S.
CitAP2.10 activation of the terpene synthase CsTPS1 is associated with the synthesis of (+)-valencene in Newhall orange
J. Exp. Bot.
67
4105-4115
2016
Citrus sinensis
brenda
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