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4.2.3.32

Accepted name:

levopimaradiene synthase

Reaction:

(+)-copalyl diphosphate = abieta-8(14),12-diene + diphosphate

For diagram of abietadiene, abietate, isopimaradiene, labdadienol and sclareol biosynthesis, click here and for diagram of abietadiene, levopimaradiene and isopimara-7,15-diene biosynthesis, click here

Glossary:

levopimaradiene = abieta-8(14),12-diene

Other name(s):

PtTPS-LAS; LPS; copalyl-diphosphate diphosphate-lyase [abieta-8(14),12-diene-forming]

Systematic name:

(+)-copalyl-diphosphate diphosphate-lyase [abieta-8(14),12-diene-forming]

Comments:

In Ginkgo, the enzyme catalyses the initial cyclization step in the biosynthesis of ginkgolides, a structurally unique family of diterpenoids that are highly specific platelet-activating-factor receptor antagonists [1]. Levopimaradiene is widely distributed in higher plants. In some species the enzyme also forms abietadiene, palustradiene, and neoabietadiene [2].

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Schepmann, H.G., Pang, J. and Matsuda, S.P. Cloning and characterization of Ginkgo biloba levopimaradiene synthase which catalyzes the first committed step in ginkgolide biosynthesis. Arch. Biochem. Biophys. 392 (2001) 263–269. [DOI] [PMID: 11488601]
2.	Ro, D.K. and Bohlmann, J. Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1). Phytochemistry 67 (2006) 1572–1578. [DOI] [PMID: 16497345]

[EC 4.2.3.32 created 2008, modified 2012]

4.2.3.44

Accepted name:

isopimara-7,15-diene synthase

Reaction:

(+)-copalyl diphosphate = isopimara-7,15-diene + diphosphate

Glossary:

isopimara-7,15-diene = 13α-pimara-7,15-diene

Other name(s):

PaTPS-Iso; copalyl diphosphate-lyase (isopimara-7,15-diene-forming)

Systematic name:

(+)-copalyl diphosphate-lyase (isopimara-7,15-diene-forming)

Comments:

The enzyme only gave isopimara-7,15-diene.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Martin, D.M., Faldt, J. and Bohlmann, J. Functional characterization of nine Norway Spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily. Plant Physiol. 135 (2004) 1908–1927. [DOI] [PMID: 15310829]

[EC 4.2.3.44 created 2009]

4.2.3.132

Accepted name:

neoabietadiene synthase

Reaction:

(+)-copalyl diphosphate = neoabietadiene + diphosphate

For diagram of abietane diterpenoids biosynthesis, click here

Glossary:

neoabietadiene = abieta-8(14),13(15)-diene

Other name(s):

TPS-LAS

Systematic name:

(+)-copaly-diphosphate diphosphate-lyase (cyclizing, neoabietadiene-forming)

Comments:

Isolated from Abies grandis (grand fir) [1]. This class I enzyme forms about equal proportions of abietadiene, levopimaradiene and neoabietadiene. See also EC 4.2.3.18, abieta-7,13-diene synthase and EC 4.2.3.32, levopimaradiene synthase. An X-ray study of this multifunctional enzyme showed that the class I activity is in the α domain, while (+)-copalyl diphosphate synthase activity (EC 5.5.1.12, a class II activity) is in the β and γ domains [2]. In Pinus taeda (loblolly pine) the major product is levopimaradiene, with less abietadiene and neoabietadiene [3].

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Peters, R.J., Flory, J.E., Jetter, R., Ravn, M.M., Lee, H.J., Coates, R.M. and Croteau, R.B. Abietadiene synthase from grand fir (Abies grandis): characterization and mechanism of action of the "pseudomature" recombinant enzyme. Biochemistry 39 (2000) 15592–15602. [DOI] [PMID: 11112547]
2.	Zhou, K., Gao, Y., Hoy, J.A., Mann, F.M., Honzatko, R.B. and Peters, R.J. Insights into diterpene cyclization from structure of bifunctional abietadiene synthase from Abies grandis. J. Biol. Chem. 287 (2012) 6840–6850. [DOI] [PMID: 22219188]
3.	Ro, D.K. and Bohlmann, J. Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1). Phytochemistry 67 (2006) 1572–1578. [DOI] [PMID: 16497345]

[EC 4.2.3.132 created 2012]