ExplorEnz: EC 1.21.3.7

Your query returned 1 entry. Printable version

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, Gene, KEGG, MetaCyc, PDB

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]