Cannabidiolic acid synthase
| Cannabidiolic acid synthase | |||||||||
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| Identifiers | |||||||||
| EC number | 1.21.3.8 | ||||||||
| Databases | |||||||||
| IntEnz | IntEnz view | ||||||||
| BRENDA | BRENDA entry | ||||||||
| ExPASy | NiceZyme view | ||||||||
| KEGG | KEGG entry | ||||||||
| MetaCyc | metabolic pathway | ||||||||
| PRIAM | profile | ||||||||
| PDB structures | RCSB PDB PDBe PDBsum | ||||||||
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Cannabidiolic acid synthase (EC 1.21.3.8, CBDA synthase) is an enzyme with systematic name cannabigerolate:oxygen oxidoreductase (cyclizing, cannabidiolate-forming).[1][2] It is an oxidoreductase found in Cannabis sativa that catalyses the formation of cannabidiolate, a carboxylated precursor of the cannabinoid Cannabidiol.[2]
Enzyme structure
Cannabidiolic acid synthase consists of a single protein with a molecular mass of 74 kDa.[1] Its amino acid sequence is partly (40-50%) homologous to several other oxidoreductases,[2] such as berberine bridge enzyme in Eschscholzia californica[3] and Nectarin V in Nicotiana langsdorffii X N. sanderae.[4]
CBDA synthase has four binding sites; two for FAD and two for the substrate.[5]
Enzyme function
Cannabidiolic acid synthase catalyses the production of cannabidiolate predominantly from cannabigerolate by stereospecific oxidative cyclization of the geranyl group of cannabigerolic acid[2] according to the following chemical reaction:
- cannabigerolate + O2
cannabidiolate + H2O2
Cannabinerolate can also be used as a substrate, but with lower efficiency (KM=0.137 mM) than cannabigerolate (KM=0.206 mM). It covalently binds FAD, and does not require coenzymes, molecular oxygen, hydrogen peroxide, or metal ion cofactors for the oxidocyclization reaction.[1]
The optimum pH for CBDA synthase is 5.0.[1]
References
- 1 2 3 4 Taura, F., Morimoto, S. and Shoyama, Y. (1996). "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. doi:10.1074/jbc.271.29.17411. PMID 8663284.
- 1 2 3 4 Taura, F., Sirikantaramas, S., Shoyama, Y., Yoshikai, K., Shoyama, Y. and Morimoto, S. (2007). "Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa". FEBS Lett 581: 2929–2934. doi:10.1016/j.febslet.2007.05.043. PMID 17544411.
- ↑ Kutchan, T.M. and Dittrich, H. (1995). "Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants". J. Biol. Chem. 270: 24475–24481. doi:10.1074/jbc.270.41.24475.
- ↑ Carter, C.J. and Thornburg, R.W. (2004). "Tobacco Nectarin V Is a Flavin-Containing Berberine Bridge Enzyme-Like Protein with Glucose Oxidase Activity". Plant Physiol. 134: 460–469. doi:10.1104/pp.103.027482.
- ↑ "CBDAS - Cannabidiolic acid synthase precursor - Cannabis sativa (Hemp) - CBDAS gene & protein". UniProt. Retrieved 26 February 2016.
External links
- Cannabidiolic acid synthase at the US National Library of Medicine Medical Subject Headings (MeSH)
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