Biology:Abietadiene synthase
| abieta-7,13-diene synthase | |||||||||
|---|---|---|---|---|---|---|---|---|---|
| Identifiers | |||||||||
| EC number | 4.2.3.18 | ||||||||
| CAS number | 157972-08-2 | ||||||||
| Databases | |||||||||
| IntEnz | IntEnz view | ||||||||
| BRENDA | BRENDA entry | ||||||||
| ExPASy | NiceZyme view | ||||||||
| KEGG | KEGG entry | ||||||||
| MetaCyc | metabolic pathway | ||||||||
| PRIAM | profile | ||||||||
| PDB structures | RCSB PDB PDBe PDBsum | ||||||||
| Gene Ontology | AmiGO / QuickGO | ||||||||
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The enzyme abieta-7,13-diene synthase (EC 4.2.3.18) catalyzes the chemical reaction
- (+)-copalyl diphosphate [math]\displaystyle{ \rightleftharpoons }[/math] abieta-7,13-diene + diphosphate
This enzyme belongs to the family of lyases, specifically those carbon-oxygen lyases acting on phosphates. The systematic name of this enzyme class is (+)-copalyl-diphosphate diphosphate-lyase [cyclizing, abieta-7,13-diene-forming]. This enzyme is also called copalyl-diphosphate diphosphate-lyase (cyclizing). This enzyme participates in diterpenoid biosynthesis.
It has recently been shown (Keeling, et al., 2011) that the orthologous gene in Norway spruce (Picea abies) does not produce abietadiene directly, but instead produces a thermally unstable allylic tertiary alcohol 13-hydroxy-8(14)- abietene, which readily dehydrates to abietadiene, levopimaradiene, palustradiene, and neoabietadiene, when analyzed by the commonly used gas chromatography. This has been confirmed in the other conifer species, lodgepole pine (Pinus contorta) and Jack pine (Pinus banksiana) (Hall et al., 2013).
References
- RB; Flory, JE; Jetter, R; Ravn, MM; Lee, HJ; Coates, RM; Croteau, RB (2000). "Abietadiene synthase from grand fir (Abies grandis): characterization and mechanism of action of the "pseudomature" recombinant enzyme". Biochemistry 39 (50): 15592–602. doi:10.1021/bi001997l. PMID 11112547.
- "Bifunctional abietadiene synthase: free diffusive transfer of the (+)-copalyl diphosphate intermediate between two distinct active sites". J. Am. Chem. Soc. 123 (37): 8974–8. 2001. doi:10.1021/ja010670k. PMID 11552804.
- "Abietadiene synthase catalysis: mutational analysis of a prenyl diphosphate ionization-initiated cyclization and rearrangement". Proc. Natl. Acad. Sci. U.S.A. 99 (2): 580–4. 2002. doi:10.1073/pnas.022627099. PMID 11805316.
- "Abietadiene synthase catalysis: conserved residues involved in protonation-initiated cyclization of geranylgeranyl diphosphate to (+)-copalyl diphosphate". Biochemistry 41 (6): 1836–42. 2002. doi:10.1021/bi011879d. PMID 11827528. https://works.bepress.com/reuben_peters/15/download/.
- "Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates". J. Am. Chem. Soc. 124 (24): 6998–7006. 2002. doi:10.1021/ja017734b. PMID 12059223.
- "The primary diterpene synthase products of Picea abies levopimaradiene/abietadiene synthase (PaLAS) are epimers of a thermally unstable diterpenol". J. Biol. Chem. 286 (24): 21145–21153. 2011. doi:10.1074/jbc.M111.245951. PMID 21518766.
- "Evolution of conifer diterpene synthases: diterpene resin acid biosynthesis in lodgepole pine and jack pine involves monofunctional and bifunctional diterpene synthases". Plant Physiol. 161 (2): 600–616. 2013. doi:10.1104/pp.112.208546. PMID 23370714.
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