The Enzyme Database

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EC 1.21.3.7     
Accepted name: tetrahydrocannabinolic acid synthase
Reaction: cannabigerolate + O2 = Δ9-tetrahydrocannabinolate + H2O2
For diagram of cannabinoid biosynthesis, click here
Glossary: Δ9-tetrahydrocannabinolate = Δ9-THCA = (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylate
cannabigerolate = CBGA = 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoate
cannabinerolate = 3-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoate
Other name(s): THCA synthase; Δ1-tetrahydrocannabinolic acid synthase
Systematic name: cannabigerolate:oxygen oxidoreductase (cyclizing, Δ9-tetrahydrocannabinolate-forming)
Comments: A flavoprotein (FAD). The cofactor is covalently bound. Part of the cannabinoids biosynthetic pathway in the plant Cannabis sativa. The enzyme can also convert cannabinerolate (the (Z)-isomer of cannabigerolate) to Δ9-THCA with lower efficiency. Whereas the product was originally called Δ1-tetrahydrocannabinolate, the recommended name according to systematic peripheral numbering is Δ9-tetrahydrocannabinolate.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Taura, F., Morimoto, S. Shoyama, Y. and Mechoulam, R. First direct evidence for the mechanism of Δ1-tetrahydrocannabinolic acid biosynthesis. J. Am. Chem. Soc. 117 (1995) 9766–9767.
2.  Sirikantaramas, S., Morimoto, S., Shoyama, Y., Ishikawa, Y., Wada, Y., Shoyama, Y. and Taura, F. The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Δ1-tetrahydrocannabinolic acid synthase from Cannabis sativa L. J. Biol. Chem. 279 (2004) 39767–39774. [DOI] [PMID: 15190053]
3.  Shoyama, Y., Takeuchi, A., Taura, F., Tamada, T., Adachi, M., Kuroki, R., Shoyama, Y. and Morimoto, S. Crystallization of Δ1-tetrahydrocannabinolic acid (THCA) synthase from Cannabis sativa. Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 61 (2005) 799–801. [DOI] [PMID: 16511162]
4.  Shoyama, Y., Tamada, T., Kurihara, K., Takeuchi, A., Taura, F., Arai, S., Blaber, M., Shoyama, Y., Morimoto, S. and Kuroki, R. Structure and function of 1-tetrahydrocannabinolic acid (THCA) synthase, the enzyme controlling the psychoactivity of Cannabis sativa. J. Mol. Biol. 423 (2012) 96–105. [DOI] [PMID: 22766313]
[EC 1.21.3.7 created 2012]
 
 
EC 1.21.3.8     
Accepted name: cannabidiolic acid synthase
Reaction: cannabigerolate + O2 = cannabidiolate + H2O2
For diagram of cannabinoid biosynthesis, click here
Glossary: cannabigerolate = CBGA = 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoate
cannabidiolate = 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoate
Other name(s): CBDA synthase
Systematic name: cannabigerolate:oxygen oxidoreductase (cyclizing, cannabidiolate-forming)
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.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Taura, F., Morimoto, S. and 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 (1996) 17411–17416. [DOI] [PMID: 8663284]
2.  Taura, F., Sirikantaramas, S., Shoyama, Y., Yoshikai, K., Shoyama, Y. and Morimoto, S. Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa. FEBS Lett. 581 (2007) 2929–2934. [DOI] [PMID: 17544411]
[EC 1.21.3.8 created 2012]
 
 
EC 2.5.1.102     
Accepted name: geranyl-pyrophosphate—olivetolic acid geranyltransferase
Reaction: geranyl diphosphate + 2,4-dihydroxy-6-pentylbenzoate = diphosphate + cannabigerolate
For diagram of cannabinoid biosynthesis, click here
Glossary: 2,4-dihydroxy-6-pentylbenzoate = olivetolate
cannabigerolate = CBGA = 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoate
cannabinerolate = 3-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoate
Other name(s): GOT (ambiguous)
Systematic name: geranyl-diphosphate:olivetolate geranyltransferase
Comments: Part of the cannabinoids biosynthetic pathway of the plant Cannabis sativa. The enzyme can also use neryl diphosphate as substrate, forming cannabinerolate.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Fellermeier, M. and Zenk, M.H. Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEBS Lett. 427 (1998) 283–285. [DOI] [PMID: 9607329]
[EC 2.5.1.102 created 2012]
 
 


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