KEGG ENZYME: 1.21.3.7

ENZYME: 1.21.3.7

Entry

EC 1.21.3.7                 Enzyme

Name

tetrahydrocannabinolic acid synthase;
THCA synthase;
Delta1-tetrahydrocannabinolic acid synthase

Class

Oxidoreductases;
Catalysing the reaction X-H + Y-H = X-Y;
With oxygen as acceptor

Sysname

cannabigerolate:oxygen oxidoreductase (cyclizing, Delta9-tetrahydrocannabinolate-forming)

Reaction(IUBMB)

cannabigerolate + O2 = Delta9-tetrahydrocannabinolate + H2O2 [RN:R12101]

Reaction(KEGG)

R12101

Substrate

cannabigerolate [CPD:C20406];
O2 [CPD:C00007]

Product

Delta9-tetrahydrocannabinolate [CPD:C21903];
H2O2 [CPD:C00027]

Comment

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 Delta9-THCA with lower efficiency. Whereas the product was originally called Delta1-tetrahydrocannabinolate, the recommended name according to systematic peripheral numbering is Delta9-tetrahydrocannabinolate.

History

EC 1.21.3.7 created 2012

Pathway

ec00999

Biosynthesis of various plant secondary metabolites

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K20501

tetrahydrocannabinolic acid synthase

Genes

CSAV:

115696884 115697880

Reference

Authors

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

Title

First direct evidence for the mechanism of Delta1-tetrahydrocannabinolic acid biosynthesis.

Journal

J Am Chem Soc 117:9766-9767 (1995)

Reference

2 [PMID:15190053]

Authors

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

Title

The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.

Journal

J Biol Chem 279:39767-74 (2004)
DOI:10.1074/jbc.M403693200

Sequence

[ag:BAC41356]

Reference

3 [PMID:16511162]

Authors

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

Title

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

Journal

Acta Crystallogr Sect F Struct Biol Cryst Commun 61:799-801 (2005)
DOI:10.1107/S1744309105023365

Reference

4 [PMID:22766313]

Authors

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

Title

Structure and function of 1-tetrahydrocannabinolic acid (THCA) synthase, the enzyme controlling the psychoactivity of Cannabis sativa.

Journal

J Mol Biol 423:96-105 (2012)
DOI:10.1016/j.jmb.2012.06.030

Sequence

[ag:BAC41356]

Other DBs

ExplorEnz - The Enzyme Database:

1.21.3.7

IUBMB Enzyme Nomenclature:

1.21.3.7

ExPASy - ENZYME nomenclature database:

1.21.3.7

BRENDA, the Enzyme Database:

1.21.3.7

DBGET integrated database retrieval system