Biology:Cannabidiolic acid synthase
| 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 | ||||||||
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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]
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 require coenzymes & molecular oxygen for the oxidocyclization reaction.[1]
The optimum pH for CBDA synthase is 5.0.[2]
References
- ↑ 1.0 1.1 1.2 "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. July 1996. doi:10.1074/jbc.271.29.17411. PMID 8663284.
- ↑ 2.0 2.1 2.2 2.3 2.4 "Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa". FEBS Letters 581 (16): 2929–34. June 2007. doi:10.1016/j.febslet.2007.05.043. PMID 17544411.
- ↑ "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. October 1995. doi:10.1074/jbc.270.41.24475. PMID 7592663.
- ↑ "Tobacco nectarin V is a flavin-containing berberine bridge enzyme-like protein with glucose oxidase activity". Plant Physiology 134 (1): 460–9. January 2004. doi:10.1104/pp.103.027482. PMID 14730073.
- ↑ "CBDAS - Cannabidiolic acid synthase precursor - Cannabis sativa (Hemp) - CBDAS gene & protein". https://www.uniprot.org/uniprot/A6P6V9.
External links
- Cannabidiolic+acid+synthase at the US National Library of Medicine Medical Subject Headings (MeSH)
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