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Information on EC 4.4.1.26 - olivetolic acid cyclase and Organism(s) Cannabis sativa and UniProt Accession I6WU39

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IUBMB Comments
Part of the cannabinoids biosynthetic pathway in the plant Cannabis sativa.
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Cannabis sativa
UNIPROT: I6WU39
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The taxonomic range for the selected organisms is: Cannabis sativa
The expected taxonomic range for this enzyme is: Cannabis sativa
Synonyms
olivetolic acid cyclase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
OAC
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
aldol condensation
-
SYSTEMATIC NAME
IUBMB Comments
3,5,7-trioxododecanoyl-CoA CoA-lyase (2,4-dihydroxy-6-pentylbenzoate-forming)
Part of the cannabinoids biosynthetic pathway in the plant Cannabis sativa.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3,5,7-trioxododecanoyl-CoA
olivetolic acid + CoA
show the reaction diagram
-
-
-
?
additional information
?
-
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
OLIAC_CANSA
101
0
12002
Swiss-Prot
other Location (Reliability: 5)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
23000
dynamic light scattering
25000
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
2 * 10000, SDS-PAGE, 2 * 12200, calculated from sequence
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
space group P3121 or P3221, with unit-cell parameters a = b = 47.3, c = 176.0 A
structure of free enzyme and in complex with olivetolic acid, to 1.32 and 1.70 A resolutions. The active-site cavity contains the pentyl-binding hydrophobic pocket and the polyketide binding site. Residues Tyr72 and His78 function as acid/base catalysts at the catalytic center. The enzyme may lack thioesterase and aromatase activities
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
F24L
49% of wild-type activity
H5L
36% of wild-type activity
H5Q
22% of wild-type activity
H5S
47% of wild-type activity
H78N
0% of wild-type activity
H78Q
0% of wild-type activity
H78S
0% of wild-type activity
I7F
64% of wild-type activity
I7L
85% of wild-type activity
V59M
65% of wild-type activity
Y27F
162% of wild-type activity
Y27L
48% of wild-type activity
Y27M
30% of wild-type activity
Y27W
37% of wild-type activity
Y72F
0% of wild-type activity
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant protein
Talon resin column chromatography
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expression in Escherichia coli
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
synthesis of olivetolic acid from a single carbon source through combining OLA synthase and OLA cyclase expression with the required modules of a beta-oxidation reversal for hexanoyl-CoA generation. The use of additional auxiliary enzymes to increase hexanoyl-CoA and malonyl-CoA, along with evaluation of varying fermentation conditions, enables the synthesis of 80 mg/L olivetolic acid
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Gagne, S.; Stout, J.; Liu, E.; Boubakir, Z.; Clark, S.; Page, J.
Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides
Proc. Natl. Acad. Sci. USA
109
12811-12816
2012
Cannabis sativa (I6WU39), Cannabis sativa
Manually annotated by BRENDA team
Tan, Z.; Clomburg, J.M.; Gonzalez, R.
Synthetic pathway for the production of olivetolic acid in Escherichia coli
ACS Synth. Biol.
7
1886-1896
2018
Cannabis sativa (I6WU39)
Manually annotated by BRENDA team
Yang, X.; Matsui, T.; Mori, T.; Taura, F.; Noguchi, H.; Abe, I.; Morita, H.
Expression, purification and crystallization of a plant polyketide cyclase from Cannabis sativa
Acta Crystallogr. Sect. F
71
1470-1474
2015
Cannabis sativa (I6WU39)
-
Manually annotated by BRENDA team
Yang, X.; Matsui, T.; Kodama, T.; Mori, T.; Zhou, X.; Taura, F.; Noguchi, H.; Abe, I.; Morita, H.
Structural basis for olivetolic acid formation by a polyketide cyclase from Cannabis sativa
FEBS J.
283
1088-1106
2016
Cannabis sativa (I6WU39), Cannabis sativa
Manually annotated by BRENDA team