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Information on EC 1.21.3.8 - cannabidiolic acid synthase

for references in articles please use BRENDA:EC1.21.3.8

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EC Tree

1 Oxidoreductases

1.21 Catalysing the reaction X-H + Y-H = X-Y

1.21.3 With oxygen as acceptor

1.21.3.8 cannabidiolic acid synthase

IUBMB Comments

Binds FAD covalently. Part of the cannabinoids biosynthetic pathway of the plant Cannabis sativa. The enzyme can also convert cannabinerolate to cannabidiolate with lower efficiency.

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1.21.3.8
ubiquitin-conjugating
cannabis
cannabinoids
thcas
anaphase-promoting
hemp

The expected taxonomic range for this enzyme is: Cannabis sativa

Reaction Schemes

Synonyms

cbda synthase, cbdas, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

cannabidiolic-acid synthase

CBDA synthase

CBDA-synthase

CBDAS

CBDA synthase

CBDA synthase

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

cannabigerolate + O2 = cannabidiolate + H2O2

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Go to Pathway Search

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PATHWAY SOURCE

PATHWAYS

KEGG

Biosynthesis of secondary metabolites - unclassified

MetaCyc

cannabinoid biosynthesis

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SYSTEMATIC NAME

IUBMB Comments

cannabigerolate:oxygen oxidoreductase (cyclizing, cannabidiolate-forming)

Binds FAD covalently. Part of the cannabinoids biosynthetic pathway of the plant Cannabis sativa. The enzyme can also convert cannabinerolate to cannabidiolate with lower efficiency.

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

cannabigerolate + O2

cannabidiolate + H2O2

4 entries

cannabinerolate + O2

cannabidiolate + H2O2

Cannabis sativa

719786

additional information

Cannabis sativa

the enzyme does not require molecular oxygen for the production of cannabidiolate in the presence or absence of NADPH

719786

cannabigerolate + O2

cannabidiolate + H2O2

Cannabis sativa

745901

cannabigerolate + O2

cannabidiolate + H2O2

Cannabis sativa

A6P6V9

719489

cannabigerolate + O2

cannabidiolate + H2O2

Cannabis sativa

A0A0E3XIC7

746002

cannabigerolate + O2

cannabidiolate + H2O2

Cannabis sativa

best substrate

719786

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

cannabigerolate + O2

cannabidiolate + H2O2

2 entries

cannabigerolate + O2

cannabidiolate + H2O2

Cannabis sativa

745901

cannabigerolate + O2

cannabidiolate + H2O2

Cannabis sativa

A0A0E3XIC7

746002

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COFACTOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

FAD

Cannabis sativa

A6P6V9

the enzyme has a covalently bound flavin

719489

additional information

Cannabis sativa

the enzyme does not require any coenzyme like NAD+, NADP+, FAD, and FMN

719786

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METALS and IONS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

additional information

Cannabis sativa

the enzyme does not require metal ions

719786

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

Hg2+

Cannabis sativa

complete inhibition at 2 mM

719786

additional information

Cannabis sativa

EDTA has little influence on the enzyme activity at concentrations up to 5 mM

719786

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.137

cannabigerolate

Cannabis sativa

in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719786

0.206

cannabinerolate

Cannabis sativa

in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719786

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TURNOVER NUMBER [1/s]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.19

cannabigerolate

Cannabis sativa

in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719786

0.03

cannabinerolate

Cannabis sativa

in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719786

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SPECIFIC ACTIVITY [µmol/min/mg]

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

0.175

Cannabis sativa

enzyme from supernatant, in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719786

Cannabis sativa

after 519fold purification, in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719786

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Cannabis sativa

719786

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pH RANGE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

4 - 6

Cannabis sativa

half-maximal activities at pH values around 4.0 and 6.0

719786

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pI VALUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

6.1

Cannabis sativa

isoelectric focusing

719786

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

UniProt

brenda

Cannabis sativa

CBDA and Mexican strains

brenda

CBDA strain

UniProt

brenda

Cannabis sativa

cultivars Skunk #1 and Carmen

745901

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

brenda

Go to AA Sequence and Transmembrane Helices Search

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UNIPROT

ENTRY NAME

ORGANISM

NO. OF AA

NO. OF TRANSM. HELICES

MOLECULAR WEIGHT[Da]

SOURCE

Sequence

A6P6V9 pBLAST

CBDAS_CANSA

Cannabis sativa

544

62237

Swiss-Prot

Show Sequence

A0A084G6X6 pBLAST

A0A084G6X6_9PEZI

Scedosporium apiospermum

125

13506

TrEMBL

Show Sequence

A0A2P6R0P3 pBLAST

A0A2P6R0P3_ROSCH

Rosa chinensis

10673

TrEMBL

Show Sequence

A0A2P6Q6N0 pBLAST

A0A2P6Q6N0_ROSCH

Rosa chinensis

189

21163

TrEMBL

Show Sequence

A0A0E3XIC7 pBLAST

A0A0E3XIC7_CANSA

Cannabis sativa

544

62168

TrEMBL

Show Sequence

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MOLECULAR WEIGHT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

58863

Cannabis sativa

A6P6V9

x * 58863, deduced from amino acid sequence

62000

x * 62000, SDS-PAGE

74000

1 * 74000, SDS-PAGE

75000

gel filtration

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SUBUNIT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Cannabis sativa

A6P6V9

x * 58863, deduced from amino acid sequence; x * 62000, SDS-PAGE

monomer

1 * 74000, SDS-PAGE

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POSTTRANSLATIONAL MODIFICATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

glycoprotein

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PROTEIN VARIANTS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

H114A

inactive

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STORAGE STABILITY

ORGANISM

UNIPROT

LITERATURE

-20°C, 40% (v/v) glycerol, ineffective storage conditions for enzyme stabilization

Cannabis sativa

719786

4°C, purified enzyme in 10 mM sodium phosphate buffer (pH 7.0), 3 mM beta-mercaptoethanol, 2 weeks, 10-20% loss of activity

Cannabis sativa

719786

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PURIFICATION/commentary

ORGANISM

UNIPROT

LITERATURE

ammonium sulfate precipitation, DEAE-cellulose column chromatography, phenyl-Sepharose CL-4B column chromatography, and hydroxylapatite column chromatography

Cannabis sativa

719786

hydroxylapatite column chromatography

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CLONED/commentary

ORGANISM

UNIPROT

LITERATURE

expressed in Sf9 insect cells

Cannabis sativa

A6P6V9

719489

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

719489

Taura, F.; Sirikantaramas, S.; Shoyama, Y.; Yoshikai, K.; Shoyama, Y.; Morimoto, S.

Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa

FEBS Lett.

581

2929-2934

2007

Cannabis sativa (A6P6V9), Cannabis sativa

17544411

brenda

719786

Taura, F.; Morimoto, S.; Shoyama, Y.

Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L.. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid

J. Biol. Chem.

271

17411-17416

1996

Cannabis sativa

8663284

brenda

745901

Weiblen, G.D.; Wenger, J.P.; Craft, K.J.; ElSohly, M.A.; Mehmedic, Z.; Treiber, E.L.; Marks, M.D.

Gene duplication and divergence affecting drug content in Cannabis sativa

New Phytol.

208