Cannabidiolic acid synthase

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Cannabidiolic acid synthase
Identifiers
EC no. 1.21.3.8
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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 cannabidiol. [2]

Contents

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 + O2cannabidiolate + 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 require coenzymes & molecular oxygen for the oxidocyclization reaction. [1]

The optimum pH for CBDA synthase is 5.0. [2]

Related Research Articles

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References

  1. 1 2 3 Taura F, Morimoto S, Shoyama Y (July 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". The Journal of Biological Chemistry. 271 (29): 17411–6. doi: 10.1074/jbc.271.29.17411 . PMID   8663284.
  2. 1 2 3 4 5 Taura F, Sirikantaramas S, Shoyama Y, Yoshikai K, Shoyama Y, Morimoto S (June 2007). "Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa". FEBS Letters. 581 (16): 2929–34. doi: 10.1016/j.febslet.2007.05.043 . PMID   17544411.
  3. Kutchan TM, Dittrich H (October 1995). "Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants". The Journal of Biological Chemistry. 270 (41): 24475–81. doi: 10.1074/jbc.270.41.24475 . PMID   7592663.
  4. Carter CJ, Thornburg RW (January 2004). "Tobacco nectarin V is a flavin-containing berberine bridge enzyme-like protein with glucose oxidase activity". Plant Physiology. 134 (1): 460–9. doi:10.1104/pp.103.027482. PMC   316325 . PMID   14730073.
  5. "CBDAS - Cannabidiolic acid synthase precursor - Cannabis sativa (Hemp) - CBDAS gene & protein". UniProt. Retrieved 26 February 2016.