Cannabidiolic acid synthase

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Cannabidiolic acid synthase
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Cannabidiolic acid synthase (EC, 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[edit]

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[edit]

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]


  1. ^ a b c d Taura, F.; Morimoto, S.; 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. PMID 8663284. doi:10.1074/jbc.271.29.17411. 
  2. ^ a b c d Taura, F.; Sirikantaramas, S.; Shoyama, Y.; Yoshikai, K.; Shoyama, Y.; Morimoto, S. (2007). "Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa". FEBS Lett. 581: 2929–2934. PMID 17544411. doi:10.1016/j.febslet.2007.05.043. 
  3. ^ Kutchan, T.M.; 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. PMID 7592663. doi:10.1074/jbc.270.41.24475. 
  4. ^ Carter, C.J.; 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. PMC 316325Freely accessible. PMID 14730073. doi:10.1104/pp.103.027482. 
  5. ^ "CBDAS - Cannabidiolic acid synthase precursor - Cannabis sativa (Hemp) - CBDAS gene & protein". UniProt. Retrieved 26 February 2016. 

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