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Information on EC 1.14.19.5 - acyl-CoA 11-(Z)-desaturase and Organism(s) Choristoneura rosaceana and UniProt Accession Q8ISS3

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IUBMB 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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Choristoneura rosaceana
UNIPROT: Q8ISS3
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The taxonomic range for the selected organisms is: Choristoneura rosaceana
The enzyme appears in selected viruses and cellular organisms
Synonyms
desat1, acyl-coa desaturase, tpdesn, delta11-myristoyl-coa desaturase, z/e11-desaturase, acyl-coa delta11-desaturase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
acyl-CoA Z/E11 desaturase
UniProt
CroDELTA11 desaturase
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DELTA11 desaturase
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DELTA11-desaturase
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DELTA11-palmitoyl-coenzyme A desaturase
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fatty acid DELTA11-desaturase
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(Z)-11 myristoyl CoA desaturase
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desaturase, myristoly coenzyme A (E)-11
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myristoyl-CoA 11-(Z) desaturase
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additional information
cf. EC 1.14.19.24
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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oxidation
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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.
CAS REGISTRY NUMBER
COMMENTARY hide
199543-17-4
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77000-04-5
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
methyl myristate + reduced electron acceptor + O2
methyl (11E)-tetradec-11-enoate + methyl (11Z)-tetradec-11-enoate + acceptor + H2O
show the reaction diagram
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in the ratio 7:1
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?
myristic acid + 2 ferrocytochrome b5 + O2 + 2 H+
(Z)-11-tetradecenoate + (E)-11-tetradecenoate + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
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?
additional information
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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
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?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
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
show the reaction diagram
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-
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
topological model of CroD11 desaturase spanning the endoplasmic reticulum membrane
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
the enzyme belongs to the fatty acid desaturase type 1 family
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
ACO11_CHORO
335
5
38785
Swiss-Prot
other Location (Reliability: 4)
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
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
Q33E
site-directed mutagenesis, inactive mutant
S109A
site-directed mutagenesis, inactive mutant
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
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme expression in Saccharomyces cerevisiae double deficient ole1 elo1 strain
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hao, G.; O'Connor, M.; Liu, W.; Roelofs, W.L.
Characterization of Z/E11- and Z9-desaturases from the obliquebanded leafroller moth, Choristoneura rosaceana
J. Insect Sci.
2
26
2002
Choristoneura rosaceana (Q8ISS3), Choristoneura rosaceana
Manually annotated by BRENDA team
Ding, B.J.; Carraher, C.; Loefstedt, C.
Sequence variation determining stereochemistry of a DELTA11 desaturase active in moth sex pheromone biosynthesis
Insect Biochem. Mol. Biol.
74
68-75
2016
Choristoneura rosaceana (Q8ISS3)
Manually annotated by BRENDA team