KEGG ORTHOLOGY: K14041

ORTHOLOGY: K14041

Entry

K14041            Tight     KO

Symbol

TPS-LAS, LPS

Name

levopimaradiene/copalyl diphosphate synthase [EC:4.2.3.32 5.5.1.12]

Pathway

map00904

Diterpenoid biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Reaction

R06298

(+)-copalyl-diphosphate lyase (decyclizing)

R06302

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

R06304

(+)-copalyl-diphosphate diphosphate-lyase (palustradiene-forming)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K14041  TPS-LAS, LPS; levopimaradiene/copalyl diphosphate synthase
Enzymes [BR:ko01000]
4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.32  levopimaradiene synthase
     K14041  TPS-LAS, LPS; levopimaradiene/copalyl diphosphate synthase
5. Isomerases
  5.5  Intramolecular lyases
   5.5.1  Intramolecular lyases (only sub-subclass identified to date)
    5.5.1.12  copalyl diphosphate synthase
     K14041  TPS-LAS, LPS; levopimaradiene/copalyl diphosphate synthase

Other DBs

GO:	0052678 0050559

Genes

AG:	AAL09965(LPS)

Reference

PMID:11488601

Authors

Schepmann HG, Pang J, Matsuda SP

Title

Cloning and characterization of Ginkgo biloba levopimaradiene synthase which catalyzes the first committed step in ginkgolide biosynthesis.

Journal

Arch Biochem Biophys 392:263-9 (2001)
DOI:10.1006/abbi.2001.2438

Sequence

[ag:AAL09965]

Reference

PMID:18198275

Authors

Keeling CI, Weisshaar S, Lin RP, Bohlmann J

Title

Functional plasticity of paralogous diterpene synthases involved in conifer defense.

Journal

Proc Natl Acad Sci U S A 105:1085-90 (2008)
DOI:10.1073/pnas.0709466105

Reference

PMID:15310829

Authors

Martin DM, Faldt J, Bohlmann J

Title

Functional characterization of nine Norway Spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily.

Journal

Plant Physiol 135:1908-27 (2004)
DOI:10.1104/pp.104.042028

LinkDB

ORTHOLOGY: K19571

Entry

K19571            Tight     KO

Symbol

LPS

Name

levopimaradiene/neoabietadiene/copalyl diphosphate synthase [EC:4.2.3.32 4.2.3.132 5.5.1.12]

Pathway

map00904

Diterpenoid biosynthesis

map01110

Biosynthesis of secondary metabolites

Reaction

R06298

(+)-copalyl-diphosphate lyase (decyclizing)

R06302

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

R06303

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

R06304

(+)-copalyl-diphosphate diphosphate-lyase (palustradiene-forming)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K19571  LPS; levopimaradiene/neoabietadiene/copalyl diphosphate synthase
Enzymes [BR:ko01000]
4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.32  levopimaradiene synthase
     K19571  LPS; levopimaradiene/neoabietadiene/copalyl diphosphate synthase
    4.2.3.132  neoabietadiene synthase
     K19571  LPS; levopimaradiene/neoabietadiene/copalyl diphosphate synthase
5. Isomerases
  5.5  Intramolecular lyases
   5.5.1  Intramolecular lyases (only sub-subclass identified to date)
    5.5.1.12  copalyl diphosphate synthase
     K19571  LPS; levopimaradiene/neoabietadiene/copalyl diphosphate synthase

Other DBs

GO:	0052678 0050559

Genes

AG:	AAX07435(LPS)

Reference

PMID:16497345

Authors

Ro DK, Bohlmann J

Title

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).

Journal

Phytochemistry 67:1572-8 (2006)
DOI:10.1016/j.phytochem.2006.01.011

Sequence

[ag:AAX07435]

LinkDB

ENZYME: 4.2.3.32

Entry

EC 4.2.3.32                 Enzyme

Name

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

Class

Lyases;
Carbon-oxygen lyases;
Acting on phosphates

Sysname

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

Reaction(IUBMB)

(+)-copalyl diphosphate = abieta-8(14),12-diene + diphosphate [RN:R06302]

Reaction(KEGG)

R06302;
(other) R06304

Substrate

(+)-copalyl diphosphate [CPD:C11901]

Product

abieta-8(14),12-diene [CPD:C11879];
diphosphate [CPD:C00013]

Comment

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].

History

EC 4.2.3.32 created 2008, modified 2012

Pathway

ec00904

Diterpenoid biosynthesis

ec01110

Biosynthesis of secondary metabolites

Orthology

K14041

levopimaradiene/copalyl diphosphate synthase

K19571

levopimaradiene/neoabietadiene/copalyl diphosphate synthase

Reference

1 [PMID:11488601]

Authors

Schepmann HG, Pang J, Matsuda SP

Title

Cloning and characterization of Ginkgo biloba levopimaradiene synthase which catalyzes the first committed step in ginkgolide biosynthesis.

Journal

Arch Biochem Biophys 392:263-9 (2001)
DOI:10.1006/abbi.2001.2438

Sequence

[ag:AAL09965]

Reference

2 [PMID:16497345]

Authors

Ro DK, Bohlmann J

Title

Journal

Phytochemistry 67:1572-8 (2006)
DOI:10.1016/j.phytochem.2006.01.011

Sequence

[ag:AAL09965 AAX07435]

Other DBs

ExplorEnz - The Enzyme Database:

4.2.3.32

IUBMB Enzyme Nomenclature:

4.2.3.32

ExPASy - ENZYME nomenclature database:

4.2.3.32

BRENDA, the Enzyme Database:

4.2.3.32

LinkDB

REACTION: R06304

Entry

R06304                      Reaction

Name

(+)-copalyl-diphosphate diphosphate-lyase (palustradiene-forming)

Definition

Copalyl diphosphate <=> Palustradiene + Diphosphate

Equation

C11901 <=> C11881 + C00013

Reaction class

RC01498

C11881_C11901

Enzyme

4.2.3.32

Pathway

rn00904

Diterpenoid biosynthesis

rn01110

Biosynthesis of secondary metabolites

Brite

Enzymatic reactions [BR:br08201]
4. Lyase reactions
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.32
     R06304  Copalyl diphosphate <=> Palustradiene + Diphosphate

Orthology

K14041

levopimaradiene/copalyl diphosphate synthase [EC:4.2.3.32 5.5.1.12]

K19571

levopimaradiene/neoabietadiene/copalyl diphosphate synthase [EC:4.2.3.32 4.2.3.132 5.5.1.12]

LinkDB

DBGET integrated database retrieval system