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Information on EC 1.14.19.5 - acyl-CoA 11-(Z)-desaturase
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1.14.19.5 acyl-CoA 11-(Z)-desaturaseIUBMB Comments
The enzyme introduces a cis double bond at position C-11 of saturated fatty acyl-CoAs. In moths the enzyme participates in the biosynthesis of their sex pheromones. The enzyme from the marine microalga Thalassiosira pseudonana is specific for palmitoyl-CoA (16:0) , that from the leafroller moth Choristoneura rosaceana desaturates myristoyl-CoA (14:0) , while that from the moth Spodoptera littoralis accepts both substrates . The enzyme contains three histidine boxes that are conserved in all desaturases . It is membrane-bound, and contains a cytochrome b5-like domain at the N-terminus that serves as the electron donor for the active site of the desaturase.
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Word Map
- 1.14.19.5
- drosophila
- pheromone
-
desaturases
- melanogaster
- flies
-
cuticular
-
courtship
- stearoyl-coa
- delta9-desaturase
- simulans
-
copulation
The enzyme appears in viruses and cellular organisms
Reaction Schemes
+
2
+
+
2
=
+
2
+
2
Synonyms
desat1, acyl-coa desaturase, tpdesn, z/e11-desaturase, acyl-coa delta11-desaturase, delta11-myristoyl-coa desaturase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(Z)-11 myristoyl CoA desaturase
-
-
-
-
DELTA11 desaturase
DELTA11-(Z)-desaturase
DELTA11-desaturase
DELTA11-fatty-acid desaturase
desaturase, myristoly coenzyme A (E)-11
-
-
-
-
EC 1.14.99.32
-
-
formerly
-
myristoyl-CoA 11-(Z) desaturase
-
-
-
-
Z/EDELTA11
additional information
DELTA11-desaturase
-
several DELTA11-desaturase systems: one produces a large quantitiy of (Z)-11-hexadecenoic acid and another produces (E)_11-tetradecenoic acid
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an acyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = an (11Z)-enoyl-CoA + 2 ferricytochrome b5 + 2 H2O
long-chain acyl-CoA + reduced acceptor + O2 = DELTA11-acyl-CoA + acceptor + 2 H2O
-
-
-
-
long-chain acyl-CoA + reduced acceptor + O2 = DELTA11-acyl-CoA + acceptor + 2 H2O
active site modeling
-
an acyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = an (11Z)-enoyl-CoA + 2 ferricytochrome b5 + 2 H2O
reaction involves a first slow, isotope-sensitive C11-H cleavage, with probable formation of an unstable intermediate, followed by a second fast C12-H bond removal
-
an acyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = an (11Z)-enoyl-CoA + 2 ferricytochrome b5 + 2 H2O
a single enzyme may be responsible for the formation of both (Z)- and (E)-11-tetradecanoic acids. It is also possible that two mechanistically identical discrete enzymes are involved in each desaturation
-
an acyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = an (11Z)-enoyl-CoA + 2 ferricytochrome b5 + 2 H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
oxidation
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
,
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SYSTEMATIC NAME
IUBMB Comments
acyl-CoA,ferrocytochrome b5:oxygen oxidoreductase (11,12 cis-dehydrogenating)
The enzyme introduces a cis double bond at position C-11 of saturated fatty acyl-CoAs. In moths the enzyme participates in the biosynthesis of their sex pheromones. The enzyme from the marine microalga Thalassiosira pseudonana is specific for palmitoyl-CoA (16:0) [4], that from the leafroller moth Choristoneura rosaceana desaturates myristoyl-CoA (14:0) [5], while that from the moth Spodoptera littoralis accepts both substrates [1]. The enzyme contains three histidine boxes that are conserved in all desaturases [2]. It is membrane-bound, and contains a cytochrome b5-like domain at the N-terminus that serves as the electron donor for the active site of the desaturase.
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CAS REGISTRY NUMBER
COMMENTARY
199543-17-4
-
77000-04-5
-
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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
(Z)-11-tetradecenoyl-CoA + reduced acceptor + O2
(E,E)-10,12-tetradecadienoyl-CoA + acceptor + H2O
-
(E,E)-10,12-tetradecadienoic acid is produced from (Z)-11-tetradecenoic acid by desaturation and concomitant migration of the precursor double bond
-
-
?
methyl myristate + reduced electron acceptor + O2
methyl (11E)-tetradec-11-enoate + methyl (11Z)-tetradec-11-enoate + acceptor + H2O
myristic acid + 2 ferrocytochrome b5 + O2 + 2 H+
(Z)-11-tetradecenoate + (E)-11-tetradecenoate + 2 ferricytochrome b5 + 2 H2O
-
-
-
?
myristic acid + NADH + ?
tetradec-11-enoic acid + NAD+ + ?
-
50% of the activity with palmitic acid
-
-
?
myristic acid + reduced acceptor + O2
(Z)-tetradec-11-enoic acid + (E)-tetradec-11-enoic acid + acceptor + H2O
-
-
-
?
palmitic acid + NADH + ?
(Z)-hexadec-11-enoic acid + NAD+ + ?
-
-
-
-
?
palmitic acid + reduced acceptor + O2
(Z)-11-hexadecenoic acid + acceptor + 2 H2O
-
-
-
-
?
stearic acid + NADH + ?
oleic acid + NAD+ + ?
-
18% of the activity with palmitic acid
-
-
?
stearoyl-CoA + reduced acceptor + O2
oleoyl-CoA + acceptor + 2 H2O
-
-
-
?
tetradecanoic acid + O2 + AH2
(11E)-tetradec-11-enoic acid + A + H2O
-
-
-
-
?
tridecanoyl-CoA + reduced acceptor + O2
(Z)-tridec-11-enoyl-CoA + (E)-tridec-11-enoyl-CoA + acceptor + 2 H2O
-
reaction involves a first slow, isotpe-sensitive C11-H bond cleavage, with probable formation of an unstable intermediate, followed by a second fast C12-H bond removal
-
-
?
methyl myristate + reduced electron acceptor + O2
methyl (11E)-tetradec-11-enoate + methyl (11Z)-tetradec-11-enoate + acceptor + H2O
-
-
-
-
?
methyl myristate + reduced electron acceptor + O2
methyl (11E)-tetradec-11-enoate + methyl (11Z)-tetradec-11-enoate + acceptor + H2O
-
in the ratio 7:1
-
?
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
-
-
-
?
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
-
a single enzyme may be responsible for the formation of both (Z)- and (E)-11-tetradecanoic acids. It is also possible that two mechanistically identical discrete enzymes are involved in each desaturation
-
?
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
-
enzyme is involved in the biosynthesis of Spodoptera littoralis sex pheromone
-
?
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
-
enzyme is involved in the biosynthesis of Spodoptera littoralis sex pheromone
-
?
palmitic acid + reduced acceptor + O2
(Z)-hexadec-11-enoic acid + acceptor + 2 H2O
-
pro-(R) C(11)-H and pro-(R) C(12)-H stereospecificity
-
-
?
palmitic acid + reduced acceptor + O2
(Z)-hexadec-11-enoic acid + acceptor + 2 H2O
-
pro-(R) C(11)-H and pro-(R) C(12)-H stereospecificity
-
-
?
palmitic acid + reduced acceptor + O2
(Z)-hexadec-11-enoic acid + acceptor + 2 H2O
-
-
-
?
palmitic acid + reduced acceptor + O2
hexadec-11-enoic acid + acceptor + 2 H2O
-
-
-
?
palmitic acid + reduced acceptor + O2
hexadec-11-enoic acid + acceptor + 2 H2O
enzyme is not involved in production of polyunsaturated fatty acids
-
-
?
additional information
?
-
-
the enzyme produces a mixture of Z/E11-14:acids and exhibits no activity with C16 and C18 saturated fatty acid precursors
-
-
?
additional information
?
-
-
several DELTA11-desaturase systems: one produces a large quantitiy of (Z)-11-hexadecenoic acid and another produces (E)_11-tetradecenoic acid
-
-
?
additional information
?
-
structure-function analysis determing the stereochemistry of the product formation. Residue E258 in the cytosolic carboxyl terminus of the protein is critical for the Z activity of the Choristoneura rosaceana desaturase
-
-
?
additional information
?
-
-
heterologous expression in yeast shows that Dpu-D11-LPAE produces large amounts of DELTA11-monoenoic acids, in particular the Z11-16:Me and Z11-18:Me in a 1.5:1 ratio. When supplemented with the Z9-16:Me, yeast extracts of Dpu-D112-LPAE contained no 9,11-16:Me, but contain small amounts of E9,Z11-and E9,E11-16:Me when supplemented with E9-16:Me
-
-
?
additional information
?
-
-
heterologous expression in yeast shows that Dpu-DELTA11-APSQ produces a series of mono-unsaturated products. These monoenes are identified as DELTA8-12:Me, DELTA 8-14:Me and DELTA 8-16:Me. When supplemented with the Z9-16:acid, yeast cells transformed with Dpu-DELTA11-APSQ do not produce the DELTA8-unsaturated fatty acid methyl esters, but produce significant amount of di-unsaturated 9,11-C16 methylesters
-
-
?
additional information
?
-
catalyses key reactions leading to mono- and di-unsaturated fatty acyl-moities
-
-
?
additional information
?
-
-
catalyses key reactions leading to mono- and di-unsaturated fatty acyl-moities
-
-
?
additional information
?
-
MsexAPTQ desaturase catalyses the production of Z11-hexadecenoate and (Z10,E12)- and (E10,E12)-hexadecadienoates via 1,4-desaturation of the Z11-16 substrate, in a stereospecific manner, GC-MS analysis of conjugated dienes formed by APTQ desaturase in recombinant Saccharomyces cerevisiae cells, overview
-
-
?
additional information
?
-
-
DELTA11-desaturase is involved in the biosynthesis of Z/E11-14:OAc
-
-
?
additional information
?
-
-
in the presence of tetradecanoic acid, only (E)-11-tetradecenoic acid is produced in Sf9 cells infected with recombinant baculoviruses expressing LATPG1. Sf9 cells infected with the control virus do not show DELTA11-desaturase activity
-
-
?
additional information
?
-
-
the enzyme produces a mixture of (E)-11- and (Z)-11-product
-
-
?
additional information
?
-
DELTA11-desaturase is involved in the biosynthesis of Z/E11-14:OAc
-
-
?
additional information
?
-
-
the enzyme produces a mixture of (E)-11- and (Z)-11-product
-
-
?
additional information
?
-
-
the enzyme is involved in the biosynthesis of Spodoptera littoralis sex pheromone
-
-
?
additional information
?
-
the recombinant enzyme expressed in yeast produces a mixture of E11-14:fatty acid, Z11-14:fatty acid, Z11-16:fatty acid and Z-11-18:fatty acid
-
-
?
additional information
?
-
-
substrate specificity, the enzyme catalyzes the formation of methylenecyclopropanes by enzymatic desaturation of 11-cyclopropylundecanoic acid and its disubstituted cis-and trans-derivatives 11-(cis-2-methylcyclopropyl)undecanoic acid, 11-(cis-2-ethylcyclopropyl)undecanoic acid, 11-(cis-2-propylcyclopropyl)undecanoic acid, 11-(trans-2-methylcyclopropyl)undecanoic acid, 11-(trans-2-ethylcyclopropyl)undecanoic acid, and 11-(trans-2-propylcyclopropyl)undecanoic acid, detailed overview
-
-
?
additional information
?
-
all unsaturated pheromone products are produced via a DELTA11 Z-desaturation mechanism
-
-
?
additional information
?
-
-
all unsaturated pheromone products are produced via a DELTA11 Z-desaturation mechanism
-
-
?
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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
myristic acid + 2 ferrocytochrome b5 + O2 + 2 H+
(Z)-11-tetradecenoate + (E)-11-tetradecenoate + 2 ferricytochrome b5 + 2 H2O
-
-
-
?
palmitic acid + reduced acceptor + O2
hexadec-11-enoic acid + acceptor + 2 H2O
enzyme is not involved in production of polyunsaturated fatty acids
-
-
?
stearoyl-CoA + reduced acceptor + O2
oleoyl-CoA + acceptor + 2 H2O
-
-
-
?
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
-
a single enzyme may be responsible for the formation of both (Z)- and (E)-11-tetradecanoic acids. It is also possible that two mechanistically identical discrete enzymes are involved in each desaturation
-
?
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
-
enzyme is involved in the biosynthesis of Spodoptera littoralis sex pheromone
-
?
myristoyl-CoA + reduced acceptor + O2
(Z)-11-tetradecenoyl-CoA + acceptor + 2 H2O
-
enzyme is involved in the biosynthesis of Spodoptera littoralis sex pheromone
-
?
additional information
?
-
-
heterologous expression in yeast shows that Dpu-D11-LPAE produces large amounts of DELTA11-monoenoic acids, in particular the Z11-16:Me and Z11-18:Me in a 1.5:1 ratio. When supplemented with the Z9-16:Me, yeast extracts of Dpu-D112-LPAE contained no 9,11-16:Me, but contain small amounts of E9,Z11-and E9,E11-16:Me when supplemented with E9-16:Me
-
-
?
additional information
?
-
-
heterologous expression in yeast shows that Dpu-DELTA11-APSQ produces a series of mono-unsaturated products. These monoenes are identified as DELTA8-12:Me, DELTA 8-14:Me and DELTA 8-16:Me. When supplemented with the Z9-16:acid, yeast cells transformed with Dpu-DELTA11-APSQ do not produce the DELTA8-unsaturated fatty acid methyl esters, but produce significant amount of di-unsaturated 9,11-C16 methylesters
-
-
?
additional information
?
-
catalyses key reactions leading to mono- and di-unsaturated fatty acyl-moities
-
-
?
additional information
?
-
-
catalyses key reactions leading to mono- and di-unsaturated fatty acyl-moities
-
-
?
additional information
?
-
-
DELTA11-desaturase is involved in the biosynthesis of Z/E11-14:OAc
-
-
?
additional information
?
-
DELTA11-desaturase is involved in the biosynthesis of Z/E11-14:OAc
-
-
?
additional information
?
-
-
the enzyme is involved in the biosynthesis of Spodoptera littoralis sex pheromone
-
-
?
additional information
?
-
all unsaturated pheromone products are produced via a DELTA11 Z-desaturation mechanism
-
-
?
additional information
?
-
-
all unsaturated pheromone products are produced via a DELTA11 Z-desaturation mechanism
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
-
NADPH is a less effective elctron donor. Highest activity with 1 mM of electron donors, reduced activity below
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
11-fluorotetradecanoic acid
-
50% inhibition at 1:1 substrate/inhibitor ratio
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Starvation
A combined proteomic and genetic analysis identifies a role for the lipid desaturase Desat1 in starvation-induced autophagy in Drosophila.
Starvation
The regulation of hepatic stearoyl-coenzyme A desaturase in obese-hyperglycaemic (ob/ob) mice by food intake and the fatty acid composition of the diet.
Tuberculosis
Identification of Rv3230c as the NADPH oxidoreductase of a two-protein DesA3 acyl-CoA desaturase in Mycobacterium tuberculosis H37Rv.
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
terminal abdominal segments with pheromone gland of female adults, RT-PCR
brenda
additional information
In the pheromone glands of virgin females the expression level increased continuously from eclosion to the end of the 1st day when it reaches a plateau without further significant fluctuation up to the 8th day. Characteristic daily rhythmicity in pheromone production with a maximum around 200 ng Z11-16Ac/PG
brenda
additional information
transcript levels of the DELTA11-desaturase in larvae, pupal PGs, fat body, brain and muscle tissues are below 0.1% of that in female pheromone glands, whereas expression in male genitalia is 2%, quantitative real-time PCR enzyme expression analysis, transcript expression profiling of DELTA11-desaturase in the pheromone gland, overview
brenda
additional information
-
in intersegmental membrane, 8th - 9th, in-situ hybridization
brenda
additional information
-
not in head, thorax, abdomen exclusive of the terminal abdominal segments
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
topological model of CroD11 desaturase spanning the endoplasmic reticulum membrane
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
the enzyme belongs to the fatty acid desaturase type 1 family
metabolism
physiological function
additional information
the 258E/D residue contributes to the formation of the secondary coordination sphere of the dimetal unit, along with 129D, 133D and 228N, molecular docking study, overview. This residue might be influencing the shape of the reactive cavity and may play an important role in the catalytic property of this desaturase. Residue E258 in the cytosolic carboxyl terminus of the protein is critical for the steroechmistry of activity
metabolism
-
functional expression of Dpu-DELTA11-APSQ cDNA belonging to the D11-subfamily, shows that is catalyses the formation of unsaturated fatty acyls that can be chain-shortened by beta-oxidation and subsequently reduced to the alcohol components
metabolism
-
functional expression of Dpu-DELTA11-LPAE cDNA belonging to the D11-subfamily, shows that is catalyses the formation of unsaturated fatty acyls that can be chain-shortened by beta-oxidation and subsequently reduced to the alcohol components
physiological function
-
acyl-CoA desaturases are key enzymes in the biosynthesis of species-specific mixtures of sex pheromone components
physiological function
acyl-CoA desaturases are key enzymes in the biosynthesis of species-specific mixtures of sex pheromone components
physiological function
acyl-CoA desaturases are key enzymes in the biosynthesis of species-specific mixtures of sex pheromone components for long-distance mate communication
physiological function
-
the absence of the Z isomer in the sex pheromone (E)-11-tetradecenol in Ostrinia latipennis is attributable to the strict product specificity of LATPG1
physiological function
regulation of DELTA11-desaturase gene expression in the pheromone gland of Mamestra brassicae during pheromonogenesis. The pheromone blend is composed of (11Z)-hexadecenyl acetate (Z11-16Ac) and hexadecyl acetate (16Ac) in a 93:7 ratio, release of pheromone biosynthesis activating neuropeptide (PBAN) regulates the pheromone production in the pheromone gland. In the pheromone glands of virgin females the expression level increased continuously from eclosion to the end of the 1st day when it reaches a plateau without further significant fluctuation up to the 8th day. Pheromonogenesis is regulated via de novo fatty acid synthesis
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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). DESAT_BOMMO
330
5
38077
Swiss-Prot
other Location (Reliability: 2)
ACO11_CHORO
335
5
38785
Swiss-Prot
other Location (Reliability: 4)
ACO11_SPOLI
338
4
39085
Swiss-Prot
other Location (Reliability: 5)
ACO11_TRINI
349
4
40243
Swiss-Prot
other Location (Reliability: 4)
A0A0K2GVJ8_MANSE
323
3
37977
TrEMBL
other Location (Reliability: 2)
A0A0K2GUR7_MANSE
323
5
37850
TrEMBL
other Location (Reliability: 2)
A0A0K2GV16_MANSE
344
5
39466
TrEMBL
other Location (Reliability: 4)
A0A0K2GUR3_MANSE
323
3
37837
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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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
16del_E
site-directed mutagenesis, the product E/Z isomer ratio is 33:67
A161G/T163M
site-directed mutagenesis, the product E/Z isomer ratio is 36:64
A88S
site-directed mutagenesis, the product E/Z isomer ratio is 32:68
E258D
site-directed mutagenesis, mutating the glutamic acid into aspartic acid transforms the Choristoneura rosaceana enzyme into a desaturase with Choristoneura parallela-like activity that produces an almost pure (E)-11-tetradecenoate product, the product E/Z isomer ratio is 86:14
F252L
site-directed mutagenesis, the product E/Z isomer ratio is 33:67
H116N/I118V
site-directed mutagenesis, the product E/Z isomer ratio is 42:58
I103M
site-directed mutagenesis, the product E/Z isomer ratio is 36:64
I174V
site-directed mutagenesis, the product E/Z isomer ratio is 35:65
I65V
site-directed mutagenesis, the product E/Z isomer ratio is 35:65
K286Q
site-directed mutagenesis, the product E/Z isomer ratio is 35:65
K309N
site-directed mutagenesis, the product E/Z isomer ratio is 34:66
L12M
site-directed mutagenesis, the product E/Z isomer ratio is 31:69
L19W
site-directed mutagenesis, the product E/Z isomer ratio is 34:66
L69I
site-directed mutagenesis, the product E/Z isomer ratio is 30:70
M250I/T251A
site-directed mutagenesis, the product E/Z isomer ratio is 35:65
N259S
site-directed mutagenesis, the product E/Z isomer ratio is 31:69
T95A
site-directed mutagenesis, the product E/Z isomer ratio is 35:65
V321I
site-directed mutagenesis, the product E/Z isomer ratio is 35:65
W45G
site-directed mutagenesis, the product E/Z isomer ratio is 31:69
additional information
-
a second non-functional ezi-inserted desaturase gene exists in Ostrinia nubilalis. The non-functionality of ezi-inserted desaturase genes may not be a direct consequence of the insertion of an ezi- or ezi-like element into the gene
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STORAGE STABILITY
ORGANISM </
</