Information on EC 4.2.3.13 - (+)-delta-cadinene synthase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY
4.2.3.13
-
RECOMMENDED NAME
GeneOntology No.
(+)-delta-cadinene synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(2E,6E)-farnesyl diphosphate = (+)-delta-cadinene + diphosphate
show the reaction diagram
the sesquiterpenoid (+)-delta-cadinene is an intermediate in phytoalexin biosynthesis. Mg2+ is required for activity
-
-
-
(2E,6E)-farnesyl diphosphate = (+)-delta-cadinene + diphosphate
show the reaction diagram
cyclization reaction
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
cyclization
-
elimination of diphosphate
elimination of diphosphate
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
gossypol biosynthesis
-
lacinilene C biosynthesis
-
Metabolic pathways
-
Sesquiterpenoid and triterpenoid biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl diphosphate diphosphate-lyase (cyclizing, (+)-delta-cadinene-forming)
The sesquiterpenoid (+)-delta-cadinene is an intermediate in phytoalexin biosynthesis. Mg2+ is required for activity.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
(+)-delta-cadinene synthase
-
-
(+)-delta-cadinene synthase isoenzyme XC1
Q39761
-
2-trans,6-trans-farnesyl-diphosphate diphosphate-lyase (cyclizing, (+)-alpha-cadinene-forming)
-
-
-
-
cadinene synthase
Q4U3F6
-
Cop4
Coprinopsis cinerea 9/55
-
-
-
cyclase, delta-cadinene
-
-
-
-
delta-cadinene cyclase
-
-
-
-
delta-cadinene synthase
-
-
-
-
delta-cadinene synthase
-
-
delta-cadinene synthase
Coprinopsis cinerea 9/55
-
-
-
EC 4.6.1.11
-
-
formerly
-
farnesyl diphosphate-delta-cadinene cyclase
-
-
-
-
sesquiterpene synthase
Q4U3F6
-
TPS2
Q4U3F6
isoform
CAS REGISTRY NUMBER
COMMENTARY
166800-09-5
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
cv. Nanking
SwissProt
Manually annotated by BRENDA team
cv. Nanking; tree cotton
-
-
Manually annotated by BRENDA team
cv. Nanking; tree cotton
Uniprot
Manually annotated by BRENDA team
cv. Nanking; tree cotton; two enzyme forms CAD1-A and CAD1-C1
-
-
Manually annotated by BRENDA team
tree cotton
SwissProt
Manually annotated by BRENDA team
cv. Seabrook 12B2; sea island cotton
-
-
Manually annotated by BRENDA team
resistant to Verticillium dahliae; sea island cotton
-
-
Manually annotated by BRENDA team
sea island cotton
-
-
Manually annotated by BRENDA team
cv. Coker 312; upland cotton
-
-
Manually annotated by BRENDA team
cv. GL-5; cv. Sumian-6; upland cotton
-
-
Manually annotated by BRENDA team
cv. GL-5; upland cotton
-
-
Manually annotated by BRENDA team
glandless line WbMgl; upland cotton
-
-
Manually annotated by BRENDA team
susceptible to Verticillium dahliae; upland cotton
-
-
Manually annotated by BRENDA team
; isoform TPS2; cultivar HA300
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
show the reaction diagram
-
-
major product
-
?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
show the reaction diagram
Q4U3F6
-
delta-cadinene is one of the two main products, while alpha-muuorlene, beta-caryophyllene, alpha-humulene and alpha-copaene are minor products
-
?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
show the reaction diagram
Coprinopsis cinerea 9/55
-
-
major product
-
?
(2E,6E)-farnesyl diphosphate + H2O
delta-cadinene + diphosphate
show the reaction diagram
Coprinopsis cinerea, Coprinopsis cinerea 9/55
-
Cop4 generates a tertiary cadinyl cation which upon deprotonation yields its major cyclization product delta-cadinene. The cadinyl cation reacts further to yield other cyclization products (beta-cubebene, cubebol , beta-copaene, sativene)
-
-
?
(2E,6Z)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-, Q39761
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
Q39761
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
Q39760, Q39761
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
nerolidyl diphosphate is an intermediate
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
transcription of cad1-C is activated in stems treated with Verticillium dahliae
-
-
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
Q39760, Q39761
the fungal-elicited production of a (+)-delta-cadinene synthase is consistent with a role for this enzyme as the first committed step in the pathways leading to the related phytoalexins gossypol and lacinilene C in cotton
-
-
-
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
the first step enzyme in the conversion of farnesyl diphosphate to sesquiterpene phytoalexins. The reaction is induced by the infection of cotton with Verticillium dahliae
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
amount of enzyme does not increase significantly in stems treated with Verticillium dahliae due to a high basal level of enzyme in untreated stems
-
-
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
the sesquiterpenoid (+)-alpha-cadinene is an intermediate in phytoalexin biosynthesis
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
the product (+)-delta-cadinene is metabolically converted to deoxyhemigossypol, deoxyhemigossypol 6-methyl ether, hemigossypol and hemigossypol 6-methyl ether
-
?
nerolidyl diphosphate
(+)-delta-cadinene + alpha-bisabolol + beta-bisabolene + beta-farnesene + ?
show the reaction diagram
Q39761
-
-
?
nerolidyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
the enzyme is encoded by a complex gene family that based on homology can be divided into two subfamilies, cad1-A and cad1-C
-
-
additional information
?
-
Q4U3F6
-
products (in vivo expression in Saccharomyces cerevisiae): delta-cadinene and a compound with a cadinene skeleton, minor products: alpha-muurolene, beta-caryophyllene, alpha-humulene and alpha-copaene
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
Q39761
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
transcription of cad1-C is activated in stems treated with Verticillium dahliae
-
-
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
Q39760, Q39761
the fungal-elicited production of a (+)-delta-cadinene synthase is consistent with a role for this enzyme as the first committed step in the pathways leading to the related phytoalexins gossypol and lacinilene C in cotton
-
-
-
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
the first step enzyme in the conversion of farnesyl diphosphate to sesquiterpene phytoalexins. The reaction is induced by the infection of cotton with Verticillium dahliae
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
amount of enzyme does not increase significantly in stems treated with Verticillium dahliae due to a high basal level of enzyme in untreated stems
-
-
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
the sesquiterpenoid (+)-alpha-cadinene is an intermediate in phytoalexin biosynthesis
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
the product (+)-delta-cadinene is metabolically converted to deoxyhemigossypol, deoxyhemigossypol 6-methyl ether, hemigossypol and hemigossypol 6-methyl ether
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
show the reaction diagram
-
the enzyme is encoded by a complex gene family that based on homology can be divided into two subfamilies, cad1-A and cad1-C
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
-
15 mM MgCl2 required for optimal activity, enzyme form CAD1-C; 2.5 mM MgCl2 required for optimal activity, enzyme form CAD1-A
Mg2+
Q39760, Q39761
required; required
Mg2+
-, Q39761
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2-fluorofarnesyl diphosphate
-, Q39761
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0024
-
(2E,6Z)-farnesyl diphosphate
-, Q39761
D451A mutant protein
0.0031
-
(2E,6Z)-farnesyl diphosphate
-, Q39761
D452A mutant protein
0.0032
-
(2E,6Z)-farnesyl diphosphate
-, Q39761
wild-type protein
0.043
-
(2E,6Z)-farnesyl diphosphate
-, Q39761
D308A mutant protein
0.0017
-
2-trans,6-trans-farnesyl diphosphate
Q39760, Q39761
pH 7, 30C, fusion protein composed of the pXC1-encoded protein and the histidine leader peptide derived from pET28
-
0.00605
-
2-trans,6-trans-farnesyl diphosphate
Q39761
pH 7.5, 30C, recombinant CDN1-C1 enzyme
-
0.007
-
2-trans,6-trans-farnesyl diphosphate
-
isoenzyme CAD1-A, pH 8.7, 30C
-
0.0106
-
2-trans,6-trans-farnesyl diphosphate
-
-
-
0.00065
-
nerolidyl diphosphate
Q39761
pH 7.5, 30C, recombinant CDN1-C1 enzyme
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.01
-
(2E,6Z)-farnesyl diphosphate
-, Q39761
wild-type protein
0.012
-
(2E,6Z)-farnesyl diphosphate
-, Q39761
D308A mutant protein
0.014
-
(2E,6Z)-farnesyl diphosphate
-, Q39761
D452A mutant protein
0.043
-
(2E,6Z)-farnesyl diphosphate
-, Q39761
D451A mutant protein
0.033
-
2-trans,6-trans-farnesyl diphosphate
Q39760, Q39761
fusion protein composed of the pXC1-encoded protein and the histidine leader peptide derived from pET28, pH 7, 30C
-
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.03
-
2-fluorofarnesyl diphosphate
-, Q39761
0.01 mM farnesyl diphosphate
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.0000487
-
-
[3H] farnesyl diphosphate
0.000405
-
-
27 days postanthesis
0.0005
-
-
60 days postanthesis
0.000746
-
-
35 days postanthesis
0.000988
-
-
40 days postanthesis
0.021
-
-
CAD1-A isozyme, expressed in Escherichia coli
0.03
-
Q39760, Q39761
recombinant protein
0.036
-
-
CAD1-A isozyme, removal of 15 amino acids by thrombin cleavage
additional information
-
-
in the early stages of infection with a defoliating isolate of the pathogen Verticillium dahliae, the enzyme activity in resistant plants increases more quickly than in susceptible plants
additional information
-
-
in roots the activity increases on day 7 post germination. In cotyledons and hypocotyls the activity decreases on day 7 post germination
additional information
-
-
enzyme activity appears between 26 and 33 days postanthesis, reaches a maximum at 38 days postanthesis and then sharply declines
additional information
-
O49853
specific activity of the enzyme increases concomitantly with the cad1 transcripts in developing cottonseeds
additional information
-
-
specific activity of the enzyme increases concomitantly with the cad1 transcripts in developing cottonseeds
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.7
8
Q39760, Q39761
;
7
7.5
-
enzyme form CAD1-C
8.7
-
-
enzyme form CAD1-A
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.8
8.7
-
62% of maximal activity at pH 6.8, enzyme form CAD1-A
7
8.7
-
60% of maximal activity at pH 8.7, enzyme form CAD1-C
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
Q39760, Q39761
time-dependent 10fold increase in mRNA in response to a challenge by preparation from Verticillium dahliae
Manually annotated by BRENDA team
-
stimulated to produce sesquiterpenoid phytoalexins by inoculation with Xanthomonas campestris pv. malvacearum, or by injection of oligogalacturonide elicitor
Manually annotated by BRENDA team
Q4U3F6
only young leaf
Manually annotated by BRENDA team
-
infected with Verticillium dahliae. Verticillium dahliae initiates a signal in the stele tissue that results in an increased steady-state level of delta-cadinene synthase mRNA and an increased activity of delta-cadinene synthase
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
45000
-
-
gel filtration
64000
-
-
SDS-PAGE
64060
-
-
calculated from DNA sequence, CAD1-A isozyme
64100
-
Q39760, Q39761
calculated from DNA sequence
64120
-
Q39760, Q39761
calculated from DNA sequence
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
Q4U3F6
x * 64200, calculated; x * 64200, calculated from amino acid sequence
monomer
-
1 * 64000-65000, SDS-PAGE
monomer
-, Q39761
1 * 64000, gel filtration, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
hanging drop vapor diffusion method
-, Q39761
modeled from amino acid sequence of CDN1-C1, in SWISS-MODEL automated homology modeling server
Q39761
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
loss of activity during freezing and thawing is gradually restored during incubation at 0C, complete recovery after 4-5 h
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, stable for at least 4 weeks
-
-20C, stable for at least 1 year
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
affinity chromatography, chromatography on glutathione-Sepharose-4B column and anion-exchange column
Q39761
CAD1-A isoenzyme
-
purification of a recombinant enzyme using histidine affinity chromatography; purification of a recombinant enzyme using histidine affinity chromatography
Q39760, Q39761
soluble at pH 11.6, ion exchange chromatography (DEAE), gel filtration
-, Q39761
N-terminal fusion of 10x His-tag, purification by affinity chromatography under native and denaturing conditions
-
slurry homogenization and centrifugation
-
to homogeneity, several chromatographic steps, including hydroxyapatite, phenyl-agarose and anion-exchange chromatography
-
Ni-NTA affinity chromatography; Ni-NTA affinity column chromatography
Q4U3F6
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed in Escherichia coli; expressed in Escherichia coli BL21(DE3) cells
-
expressed in Escherichia coli
-, Q39761
expression in Escherichia coli
O49853
expression in Escherichia coli of a cDNA isolated and amplified from a cell culture infected with Verticillium dahliae; expression in Escherichia coli of a cDNA isolated and amplified from a cell culture infected with Verticillium dahliae
Q39760, Q39761
expression in Escherichia coli of CDN1-C1
Q39761
expression in Escherichia coli of the CAD1-A isoenzyme, 80% of homology with CAD1-C isoenzyme
-
expressed in Escherichia coli
-
expressed in Saccharomyces cerevisiae strain EPY300 as a thioredoxin-fusion protein; thioredoxin-fusion protein expressed in Escherichia coli, expressed in Saccharomyces cerevisiae EPY300
Q4U3F6
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
D307A
-, Q39761
aspartate-rich motif interacts with putative Mg2+
D308A
-, Q39761
aspartate-rich motif interacts with putative Mg2+
D311A
-, Q39761
aspartate-rich motif interacts with putative Mg2+
D451A
-, Q39761
aspartate-rich motif interacts with putative Mg2+
D452A
-, Q39761
aspartate-rich motif interacts with putative Mg2+
E455A
-, Q39761
aspartate-rich motif interacts with putative Mg2+
L405H
-
mutation alters product selectivity from (+)-d-cadinene to germacrene D-4-ol (53%). Mutation improves the solubility of the enzyme
N403P
-
mutation significantly alters the product selectivity to germacrene D-4-ol (52%)
N403P/L405H
-
mutant maintains its specific activity and shows higher selectivity to germacrene D-4-ol in vivo (up to 93%)
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
agriculture
-
RNAi is used to disrupt gossypol biosynthesis in cotton seed tissue by interfering with the expression of the delta-cadinene synthase gene during seed development. It is possible to significantly reduce cottonseed-gossypol levels in a stable and heritable manner. The levels of gossypol and related terpenoids in the foliage and floral parts are not diminished, and thus their potential function in plant defense against insects and diseases remains untouched. A targeted genetic modification, applied to an underutilized agricultural byproduct, provides a mechanism to open up a new source of nutrition for hundreds of millions of people