Cannabidiolic acid synthase

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Cannabidiolic acid synthase
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

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[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]

References[edit]

  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. 

External links[edit]