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Information on EC 4.2.3.18 - abieta-7,13-diene synthase
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4.2.3.18 abieta-7,13-diene synthaseIUBMB Comments
Part of a bifunctional enzyme involved in the biosynthesis of abietadiene. See also EC 5.5.1.12, copalyl diphosphate synthase. Requires Mg2+.
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The enzyme appears in viruses and cellular organisms
Synonyms
pdabs, pttps-las, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(-)-abietadiene synthase
-
-
-
-
abietadiene cyclase
-
-
-
-
abietadiene synthase
cyclase, abietadiene
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-copalyl diphosphate = abieta-7,13-diene + diphosphate
-
-
-
-
(+)-copalyl diphosphate = abieta-7,13-diene + diphosphate
reactions leading from intermediate abieta-8(14)-en-13-yl cation to product are driven by the electrostatic effect of the ionized diphopshate group
(+)-copalyl diphosphate = abieta-7,13-diene + diphosphate
gas-phase and enzyme-free post-transition state direct dynamics simulation gas-phase reveal that abietadiene synthase must intervene in order to produce abietadiene selectively, steering this reaction to avoid the generation of a sevenmembered ring containing product which is formed in the enzyme-free reaction
-
(+)-copalyl diphosphate = abieta-7,13-diene + diphosphate
reaction mechanism proceeds via water quenching of the abieta-8(14)-en-13-yl carbocation, resulting in 13-hydroxy-8(14)-abietene
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
cyclization
elimination of diphosphate
-
-
-
-
cyclization
-
-
-
-
cyclization
-
bifunctional enzyme that catalyzes two sequential cyclization reactions (class I and clas II synthase reaction) in distinct active sites
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(+)-copalyl-diphosphate diphosphate-lyase [cyclizing, abieta-7,13-diene-forming]
Part of a bifunctional enzyme involved in the biosynthesis of abietadiene. See also EC 5.5.1.12, copalyl diphosphate synthase. Requires Mg2+.
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CAS REGISTRY NUMBER
COMMENTARY
157972-08-2
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(+)-copalyl diphosphate
(+-)-13-hydroxy-8(14)-abietene + diphosphate
-
-
initial product of the reaction, thermally unstable. Dehydration of the alcohol products of (+)-copalyl diphosphate, yielding the well established diterpene products levopimaradiene, abietadiene, neoabietadiene, and palustradiene, may occurr due to three conditions of the GC-MS analysis typically used for identification of diterpene synthase products: a hot injector, a hot oven temperature necessary for eluting the compounds, and the high temperature and high energy of the MS and its interface
-
?
(+)-copalyl-diphosphate
(-)-abietadiene + diphosphate
-
-
-
-
?
(+)-copalyl-diphosphate
(-)-abietadiene + levopimaradiene + neoabietadiene + palustradiene + diphosphate
(+)-copalyl-diphosphate
abieta-7,13-diene + abieta-8(14),13(15)-diene + abieta-8(14),12-diene + diphosphate
reaction intermediate is abieta-8(14)-en-13-yl cation
-
-
?
8alpha-hydroxy-17-nor copalyl diphosphate
17-normanoyl oxide + diphosphate
-
-
-
-
?
copalyl diphosphate
abietadienes + diphosphate
-
class I terpene synthase reaction
-
-
ir
geranylgeranyl diphosphate + diphosphate
(+)-copalyl diphosphate
-
-
-
?
(+)-copalyl diphosphate
abieta-7,13-diene + diphosphate
-
-
products are levopimaradiene, abieta-7,13-diene, and sandaracopimaradiene
-
?
(+)-copalyl-diphosphate
(-)-abietadiene + levopimaradiene + neoabietadiene + palustradiene + diphosphate
reaction intermediate is C8-sandaracopimaradienyl cation
bifunctional levopimaradiene/abietadiene synthase produces a mixture of diterpenes
-
?
(+)-copalyl-diphosphate
(-)-abietadiene + levopimaradiene + neoabietadiene + palustradiene + diphosphate
reaction intermediate is C8-sandaracopimaradienyl cation
bifunctional levopimaradiene/abietadiene synthase, about 47% levopimaradiene, 27% abietadiene, 22% neoabietadiene, 3% palustradiene
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(+)-copalyl-diphosphate
(-)-abietadiene + diphosphate
-
-
-
-
?
copalyl diphosphate
abietadienes + diphosphate
-
class I terpene synthase reaction
-
-
ir
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mg2+
-
terpene synthases (TPS) require divalent metal ion co-factors, typically magnesium
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Cowpox
Phage display antibodies against ectromelia virus that neutralize variola virus: Selection and implementation for p35 neutralizing epitope mapping.
Parkinson Disease
Postural sway in patients with early Parkinson's disease performing cognitive tasks while standing.
Smallpox
Phage display antibodies against ectromelia virus that neutralize variola virus: Selection and implementation for p35 neutralizing epitope mapping.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2
copalyl diphosphate
-
mutants D361A, D402A, D402E, D404N, D404A, D404E, D404N, D405A, D405E, D405N, D621A, E499A, R365A, R411A, R454A, W358A, Y520A
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
resin duct epithelial cells are the main site of diterpene biosynthesis in Sitka spruce, diterpenoid biosynthesis is induced in cortical resin duct epithelial cells early upon treatment with methyljasmonate, and immature developing traumatic resin duct epithelial cells produce levopimaradiene/abietadiene synthase
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
involved in the 2-C-methyl-D-erythritol 4-phosphate pathway
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). LAS_ABIBA
844
0
97273
Swiss-Prot
Mitochondrion (Reliability: 5)
TPSD1_PINBN
857
0
98479
Swiss-Prot
Chloroplast (Reliability: 3)
TPSD1_PINCO
857
0
98445
Swiss-Prot
Chloroplast (Reliability: 2)
TPSD2_PINCO
850
0
97780
Swiss-Prot
Chloroplast (Reliability: 3)
TPSDV_ABIGR
868
0
99536
Swiss-Prot
Chloroplast (Reliability: 1)
LEVOS_PICSI
859
0
98563
Swiss-Prot
Chloroplast (Reliability: 4)
B9S5Y0_RICCO
411
0
46930
TrEMBL
other Location (Reliability: 4)
TPSD1_PICAB
859
0
98458
Swiss-Prot
other Location (Reliability: 1)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 24% (v/v) PEG 8000, 0.1 M sodium citrate, pH 5.1, 0.1 M dibasic ammonium phosphate
homology model of the second active site of enzyme based on the structure of 5-epiaristolochene synthase from Nicotiana tabacum, Protein Data Bank ID code 5EAT
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A723S
product is switched from abietadienes to 75% isopimara-7,15-diene + 21% sandaracopimaradiene
D404A
D621A
D625A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
D766A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
D845A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
E589A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
E699A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
E773A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
E778A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
H348A/D621A
the mutant also produces 8alpha-hydroxy-copalyl diphosphate from geranylgeranyl diphosphate
N451A
this mutation reduces class II (protonation-initiated cyclization) activity about 100fold, with essentially no effect on class I (ionization-initiated cyclization) activity
N765A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
R584A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
R586A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
R762A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
S721A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
T617A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
T769A
T848A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
Y841F
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
A620T
-
130% of wild-type productivity. Products are 87% levopimaradiene, 11% abieta-7,13-diene, and 2% sandaracopimaradiene
C618N
-
20% of wild-type productivity. Products are 91% levopimaradiene, 9% abieta-7,13-diene, and traces of sandaracopimaradiene
G854T
-
140% of wild-type productivity. Products are 79% levopimaradiene, 14% abieta-7,13-diene, and 7% sandaracopimaradiene
I855L
-
70% of wild-type productivity. Products are 90% levopimaradiene, 7% abieta-7,13-diene, and 3% sandaracopimaradiene
K723S
-
180% of wild-type productivity. Products are 90% levopimaradiene, 7% abieta-7,13-diene, and 3% sandaracopimaradiene
L619F
-
150% of wild-type productivity. Products are 94% levopimaradiene, 6% abieta-7,13-diene, and traces of sandaracopimaradiene
L696Q
-
160% of wild-type productivity. Products are 86% levopimaradiene, 7% abieta-7,13-diene, and 7% sandaracopimaradiene
M593I
-
370% of wild-type productivity. Products are 83% levopimaradiene, 12% abieta-7,13-diene, and 5% sandaracopimaradiene
N838E
-
220% of wild-type productivity. Products are 92% levopimaradiene, 6% abieta-7,13-diene, and 2% sandaracopimaradiene
Y700F
-
500% of wild-type productivity. Products are 80% levopimaradiene, 15% abieta-7,13-diene, and 5% sandaracopimaradiene
Y700H
-
40% of wild-type productivity. Products are 71% levopimaradiene, traces of abieta-7,13-diene, and 29% sandaracopimaradiene
Y700M
-
500% of wild-type productivity. Products are 80% levopimaradiene, 13% abieta-7,13-diene, and 7% sandaracopimaradiene
Y700W
-
400% of wild-type productivity. Products are 85% levopimaradiene, 7% abieta-7,13-diene, and 8% sandaracopimaradiene
W679L/Y686H/A713S/V717L
products are isopimaradiene and sandaracopimaradiene
Y686H/A713S A713S
main products are isopimaradiene and sandaracopimaradiene
additional information
swapping of residues 568640 of isopimaradiene synhase to corresponding residues 560-632 of levopimaradiene/abietadiene synthase results in complete reversion of the product profiles of the two enzymes
D621A
this substitution eliminates the subsequently acting class I activity
T769A
-
no effect on geranylgeranyl diphosphate reaction, but lower turnover with copalyl diphosphate than wild-type
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80°C, purified enzyme in 10 mM Bis-Tris, pH 6.8, 10% (v/v) glycerol,150 mM KCl, 10 mM MgCl2, and 5 mM dithiohtreitol, several months, without significant loss of activity
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Mono Q column chromatography and type II ceramic hydroxyapatite column chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
Site-directed mutagenesis is carried out via PCR amplification with overlapping mutagenic primers, and the mutant genes verify by complete sequencing. The resulting wild type and mutant genes are then transferred via directional recombination to the T7-promoter and N-terminal 6his fusion expression vector pDEST17. Use of the pDEST17 vector results in a 25 amino acid residue linker between the 6 His-tag and the cloned protein.
-
transfection to Arabidopsis thaliana, expression in Escherichia coli mutants
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
decrease of transcript levels until third day after treatment of trees with 1 mM methyl jasmonate
transcript levels 2- or 3fold higher in wood than in other tissues and organs, increase of transcript levels one day after mechanical wounding
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
increase of levopimaradiene synthesis in Escherichia coli by amplification of the flux toward isopentenyl diphosphate and dimethylallyl diphosphate precursors and reprogramming the rate-limiting downstream pathway by generating combinatorial mutations in geranylgeranyl diphosphate synthase and levopimaradiene synthase. The most productive pathway, combining precursor flux amplification and mutant synthases, confers approximately 2600fold increase in levopimaradiene levels. A maximum titer of approximately 700 mg/l is obtained by cultivation in a benchscale bioreactor
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ravn, M.M.; Coates, R.M.; Flory, J.E.; Peters, R.J.; Croteau, R.
Stereochemistry of the cyclization-rearrangement of (+)-copalyl diphosphate to (-)-abietadiene catalyzed by recombinant abietadiene synthase from Abies grandis
Org. Lett.
2
573-576
2000
Abies grandis
brenda
Peters, R.J.; Flory, J.E.; Jetter, R.; Ravn, M.M.; Lee, H.J.; Coates, R.M.; Croteau, R.B.
Abietadiene synthase from grand fir (Abies grandis): characterization and mechanism of action of the "pseudomature" recombinant enzyme
Biochemistry
39
15592-15602
2000
Abies grandis
brenda
Peters, R.J.; Ravn, M.M.; Coates, R.M.; Croteau, R.B.
Bifunctional abietadiene synthase: Free diffusive transfer of the (+)-copalyl diphosphate intermediate between two distinct active sites
J. Am. Chem. Soc.
123
8974-8978
2001
Abies grandis
brenda
Peters, R.J.; Croteau, R.B.
Abietadiene synthase catalysis: conserved residues involved in protonation-initiated cyclization of geranylgeranyl diphosphate to (+)-copalyl diphosphate
Biochemistry
41
1836-1842
2002
Abies grandis
brenda
Peters, R.J.; Croteau, R.B.
Abietadiene synthase catalysis: mutational analysis of a prenyl diphosphate ionization-initiated cyclization and rearrangement
Proc. Natl. Acad. Sci. USA
99
580-584
2002
Abies grandis
brenda
Ravn, M.M.; Peters, R.J.; Coates, R.M.; Croteau, R.
Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates
J. Am. Chem. Soc.
124
6998-7006
2002
Abies grandis
brenda
Peters, R.J.; Carter, O.A.; Zhang, Y.; Matthews, B.W.; Croteau, R.B.
Bifunctional abietadiene synthase: mutual structural dependence of the active sites for protonation-initiated and ionization-initiated cyclizations
Biochemistry
42
2700-2707
2003
Abies grandis
brenda
Vogel, B.S.; Wildung, M.R.; Vogel, G.; Croteau, R.
Abietadiene synthase from grand fir (Abies grandis). cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase involved in resin acid biosynthesis
J. Biol. Chem.
271
23262-23268
1996
Abies grandis
brenda
Ro, D.K.; 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
1572-1578
2006
Pinus taeda, Pinus taeda (Q50EK2)
brenda
Wilderman, P.R.; Peters, R.J.
A single residue switch converts abietadiene synthase into a pimaradiene specific cyclase
J. Am. Chem. Soc.
129
15736-15737
2007
Abies grandis (Q38710)
brenda
Keeling, C.I.; Weisshaar, S.; Lin, r.P.C.; Bohlmann, J.
Functional plasticity of paralogous diterpene synthases involved in conifer defense
Proc. Natl. Acad. Sci. USA
105
1085-1090
2008
Picea abies (Q675L4)
brenda
Zhou, K.; Peters, R.J.
Investigating the conservation pattern of a putative second terpene synthase divalent metal binding motif in plants
Phytochemistry
70
366-369
2009
Abies grandis
brenda
Kim, Y.B.; Kim, S.M.; Kang, M.K.; Kuzuyama, T.; Lee, J.K.; Park, S.C.; Shin, S.C.; Kim, S.U.
Regulation of resin acid synthesis in Pinus densiflora by differential transcription of genes encoding multiple 1-deoxy-D-xylulose 5-phosphate synthase and 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase genes
Tree Physiol.
29
737-749
2009
Pinus densiflora (B9U4U8), Pinus densiflora
brenda
Siebert, M.R.; Zhang, J.; Addepalli, S.V.; Tantillo, D.J.; Hase, W.L.
The need for enzymatic steering in abietic acid biosynthesis: gas-phase chemical dynamics simulations of carbocation rearrangements on a bifurcating potential energy surface
J. Am. Chem. Soc.
133
8335-8343
2011
synthetic construct
brenda
Keeling, C.I.; Madilao, L.L.; Zerbe, P.; Dullat, H.K.; Bohlmann, J.
The primary diterpene synthase products of Picea abies levopimaradiene/abietadiene synthase (PaLAS) are epimers of a thermally unstable diterpenol
J. Biol. Chem.
286
21145-21153
2011
Picea abies
brenda
Zulak, K.G.; Dullat, H.K.; Keeling, C.I.; Lippert, D.; Bohlmann, J.
Immunofluorescence localization of levopimaradiene/abietadiene synthase in methyl jasmonate treated stems of Sitka spruce (Picea sitchensis) shows activation of diterpenoid biosynthesis in cortical and developing traumatic resin ducts
Phytochemistry
71
1695-1699
2010
Picea sitchensis
brenda
Leonard, E.; Ajikumar, P.K.; Thayer, K.; Xiao, W.H.; Mo, J.D.; Tidor, B.; Stephanopoulos, G.; Prather, K.L.
Combining metabolic and protein engineering of a terpenoid biosynthetic pathway for overproduction and selectivity control
Proc. Natl. Acad. Sci. USA
107
13654-13659
2010
Ginkgo biloba
brenda
Zhou, K.; Gao, Y.; Hoy, J.A.; Mann, F.M.; Honzatko, R.B.; Peters, R.J.
Insights into diterpene cyclization from structure of bifunctional abietadiene synthase from Abies grandis
J. Biol. Chem.
287
6840-6850
2012
Abies grandis (Q38710)
brenda
Criswell, J.; Potter, K.; Shephard, F.; Beale, M.H.; Peters, R.J.
A single residue change leads to a hydroxylated product from the class II diterpene cyclization catalyzed by abietadiene synthase
Org. Lett.
14
5828-5831
2012
Abies grandis (Q38710)
brenda
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