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Ligand cannabigerolate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.7

cannabigerolate + O2 = DELTA9-tetrahydrocannabinolate + H2O2

745424, 745428, 744452, 744573, 744759, 745421, 745476, 746002

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1.21.3.8

cannabigerolate + O2 = cannabidiolate + H2O2

745901, 746002

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In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.102

geranyl diphosphate + 2,4-dihydroxy-6-pentylbenzoate = diphosphate + cannabigerolate

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-

2.5.1.102

geranyl diphosphate + olivetolic acid = diphosphate + cannabigerolate

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-

2.5.1.102

2 entries

Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Substrate (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.3

cannabigerolic acid + O2 = cannabidiolic acid + H2O2

744172

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1.21.3.7

cannabigerolate + O2 = DELTA9-tetrahydrocannabinolate + H2O2

720263, 745424, 745428, 719489, 718487, 744452, 744573, 744759, 745421, 745476, 746002, 719821, 719637, 718732, 719343

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1.21.3.8

cannabigerolate + O2 = cannabidiolate + H2O2

745901, 719489, 746002, 719786

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Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.102

geranyl diphosphate + 2,4-dihydroxy-6-pentylbenzoate = diphosphate + cannabigerolate

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-

2.5.1.102

geranyl diphosphate + olivetolic acid = diphosphate + cannabigerolate

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-

2.5.1.102

2 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.7

substrate inhibition

745424

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (6 results)

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Show Turnover Number (6 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.21.3.7

0.043

-

mutant enzyme R108A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719821

1.21.3.7

0.075

-

mutant enzyme R110A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719821

1.21.3.7

0.3

-

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

719821

1.21.3.7

0.308

-

at pH 5.0 and 30°C

745424

1.21.3.7

0.888

-

recombinant enzyme, in 100 mM sodium citrate (pH 5.5), at 30°C

718732

1.21.3.7

5 entries

1.21.3.8

0.19

-

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

719786

K_M Value (7 results)

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Show KM Value (7 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.21.3.7

0.0084

-

at pH 5.0 and 30°C

745424

1.21.3.7

0.131

-

recombinant enzyme, in 100 mM sodium citrate (pH 5.5), at 30°C

718732

1.21.3.7

0.134

-

at pH 6.0, temperature not specified in the publication

719637

1.21.3.7

0.446

-

mutant enzyme R108A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719821

1.21.3.7

0.54

-

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

719821

1.21.3.7

0.783

-

mutant enzyme R110A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C

719821

1.21.3.7

6 entries

1.21.3.8

0.137

-

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

719786

References & Links

Literature References (18)

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Show Reference (18 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

718487

16511162

Crystallization of Delta1-tetrahydrocannabinolic acid (THCA) synthase from Cannabis sativa

2005

Shoyama, Y.; Takeuchi, A.; Taura, F.; Tamada, T.; Adachi, M.; Kuroki, R.; Shoyama, Y.; Morimoto, S.

Acta Crystallogr. Sect. F

61

799-801

718732

17669365

Production of DELTA1-tetrahydrocannabinolic acid by the biosynthetic enzyme secreted from transgenic Pichia pastoris

2007

Taura, F.; Dono, E.; Sirikantaramas, S.; Yoshimura, K.; Shoyama, Y.; Morimoto, S.

Biochem. Biophys. Res. Commun.

361

675-680

719343

22495534

Studies on tetrahydrocannabinolic acid synthase that produces the acidic precursor of tetrahydrocannabinol, the pharmacologically active cannabinoid in marijuana

2009

Taura, F.

Drug Discov. Ther.

3

83-87

719489

17544411

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

2007

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

FEBS Lett.

581

2929-2934

719637

-

First direct evidence for the mechanism of DELTA1-tetrahydrocannabinolic acid biosynthesis

1995

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

J. Am. Chem. Soc.

117

9766-9767

719786

8663284

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

1996

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

J. Biol. Chem.

271

17411-17416

719821

15190053

The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of DELTA1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.

2004

Sirikantaramas, S.; Morimoto, S.; Shoyama, Y.; Ishikawa, Y.; Wada, Y.; Shoyama, Y.; Taura, F.

J. Biol. Chem.

279

39767-39774

720263

22766313

Structure and function of DELTA1-tetrahydrocannabinolic acid (THCA) synthase, the enzyme controlling the psychoactivity of Cannabis sativa

2012

Shoyama, Y.; Tamada, T.; Kurihara, K.; Takeuchi, A.; Taura, F.; Arai, S.; Blaber, M.; Shoyama, Y.; Morimoto, S.; Kuroki, R.

J. Mol. Biol.

423

96-105

744172

28676375

The family of berberine bridge enzyme-like enzymes A treasure-trove of oxidative reactions

2017

Daniel, B.; Konrad, B.; Toplak, M.; Lahham, M.; Messenlehner, J.; Winkler, A.; Macheroux, P.

Arch. Biochem. Biophys.

632

88-103

744452

24516324

Affinity comparison of different THCA synthase to CBGA using modeling computational approaches

2014

Alaoui, M.A.; Ibrahimi, A.; Semlali, O.; Tarhda, Z.; Marouane, M.; Najwa, A.; Soulaymani, A.; Fahime, E.E.

Bioinformation

10

33-38

744573

25994576

Production of DELTA9-tetrahydrocannabinolic acid from cannabigerolic acid by whole cells of Pichia (Komagataella) pastoris expressing DELTA9-tetrahydrocannabinolic acid synthase from Cannabis sativa L.

2015

Zirpel, B.; Stehle, F.; Kayser, O.

Biotechnol. Lett.

37

1869-1875

744759

26401520

Enrichment and identification of DELTA9-tetrahydrocannabinolic acid synthase from Pichia pastoris culture supernatants

2015

Lange, K.; Poetsch, A.; Schmid, A.; Julsing, M.K.

Data Brief

4

641-649

745421

26197418

DELTA9-Tetrahydrocannabinolic acid synthase production in Pichia pastoris enables chemical synthesis of cannabinoids

2015

Lange, K.; Schmid, A.; Julsing, M.K.

J. Biotechnol.

211

68-76

745424

27369551

DELTA9-Tetrahydrocannabinolic acid synthase The application of a plant secondary metabolite enzyme in biocatalytic chemical synthesis

2016

Lange, K.; Schmid, A.; Julsing, M.K.

J. Biotechnol.

233

42-48

745428

28694184

Engineering yeasts as platform organisms for cannabinoid biosynthesis

2017

Zirpel, B.; Degenhardt, F.; Martin, C.; Kayser, O.; Stehle, F.

J. Biotechnol.

259

204-212

745476

28772109

Differentiation of Cannabis subspecies by THCA synthase gene analysis using RFLP

2017

Cirovic, N.; Kecmanovic, M.; Keckarevic, D.; Keckarevic Markovic, M.

J. Forensic Leg. Med.

51

81-84

745901

26189495

Gene duplication and divergence affecting drug content in Cannabis sativa

2015

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

New Phytol.

208

1241-1250

746002

25865737

Sequence heterogeneity of cannabidiolic- and tetrahydrocannabinolic acid-synthase in Cannabis sativa L. and its relationship with chemical phenotype

2015

Onofri, C.; de Meijer, E.P.M.; Mandolino, G.

Phytochemistry

116

57-68

Links to other databases for cannabigerolate

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Show Links (1 entry)

ChEBI

PubChem

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