Abietadiene synthase

abieta-7,13-diene synthase
Identifiers
EC no.	4.2.3.18
CAS no.	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
Search PMC articles PubMed articles NCBI proteins

The enzyme abieta-7,13-diene synthase (EC 4.2.3.18) catalyzes the chemical reaction

(+)-copalyl diphosphate ${\displaystyle \rightleftharpoons }$ 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.
• Peters RJ, Ravn MM, Coates RM, Croteau RB (2001). "Bifunctional abietadiene synthase: free diffusive transfer of the (+)-copalyl diphosphate intermediate between two distinct active sites". J. Am. Chem. Soc. 123 (37): 8974–8. doi:10.1021/ja010670k. PMID   11552804.
• Peters RJ, Croteau RB (2002). "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. doi: 10.1073/pnas.022627099 . PMC   117348 . PMID   11805316.
• Peters RJ, Croteau RB (2002). "Abietadiene synthase catalysis: conserved residues involved in protonation-initiated cyclization of geranylgeranyl diphosphate to (+)-copalyl diphosphate". Biochemistry. 41 (6): 1836–42. doi:10.1021/bi011879d. PMID   11827528.
• Ravn MM, Peters RJ, Coates RM, Croteau R (2002). "Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates". J. Am. Chem. Soc. 124 (24): 6998–7006. doi:10.1021/ja017734b. PMID   12059223.
• Keeling CI, Madilao LL, Zerbe P, Dullat HK, Bohlmann J (2011). "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. doi: 10.1074/jbc.M111.245951 . PMC   3122176 . PMID   21518766.
• Hall DE, Zerbe P, Jancsik S, Quesada AL, Dullat H, Madilao LL, Yuen M, Bohlmann J (2013). "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. doi:10.1104/pp.112.208546. PMC   3561007 . PMID   23370714.