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(3R)-linalyl diphosphate
(-)-beta-pinene + diphosphate
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene
-
?
(3R)-linalyl diphosphate
myrcene + diphosphate
-
-
-
-
?
(3S)-linalyl diphosphate
(-)-beta-pinene + diphosphate
geranyl diphosphate
(+)-beta-pinene + diphosphate
-
-
main product
-
?
geranyl diphosphate
(-)-beta-pinene
-
-
products are 28% (-)-alpha-pinene, 35% (-)-beta-pinene, 24% (+)-camphene, 5% (+)-limonene, plus some terpinolene and myrcene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
geranyl diphosphate
beta-pinene + diphosphate
neryl diphosphate
(-)-beta-pinene + diphosphate
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene
-
?
additional information
?
-
(3S)-linalyl diphosphate
(-)-beta-pinene + diphosphate
-
-
63% (-)-beta-pinene, 25.8% (+-)carene, and 6.7% alpha-pinene in almost racemic mixture.Products are exactly the same as with geranyl diphosphate
-
?
(3S)-linalyl diphosphate
(-)-beta-pinene + diphosphate
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
42% terpinolene, 18% (-)-alpha-pinene, 11% (-)-limonene, 10% (-)-beta-pinene plus several minor products
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
-
about 40% (-)-alpha-pinene and 60% (-)-beta-pinene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
products are (-)-alpha-pinene and (-)-beta pinene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
products are 29% (-)-alpha-pinene, 63% (-)-beta-pinene, 1.8% myrcene, 3.6% limonene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
-
products are 31.9% (-)-alpha-pinene and 63.9% (-)-beta-pinene, plus 4.2% myrcene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
products are (-)-alpha-pinene and (-)-beta-pinene, in a ratio of 6:94
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
products are beta-pinene (81.4%, almost exclusively (-)-beta-pinene), sabinene (11%), alpha-pinene (4.1%), limonene (3.5%) and a trace of gamma-terpinene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
products are (-)-alpha-pinene and (-)-beta-pinene, in a ratio of about 35:10
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
75.2% (-)-beta-pinene + 13.1% (-)-alpha-pinene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
80.6% (-)-beta-pinene + 8.4% (-)-alpha-pinene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
-
63% (-)-beta-pinene, 25.8% (+-)carene, and 6.7% alpha-pinene in almost racemic mixture. (+)-alpha-pinene arises from the rare isomerization of geranyl diphosphate to (3R)-linalyl diphosphate
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
76.6% (-)-alpha-pinene + 9.9% (-)-beta-pinene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
9% (-)-alpha-pinene + 79% (-)-beta-pinene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
-
25% (-)-alpha-pinene, 31% (-)-camphene, 24% (-)beta-pinene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
-
main products are (-)-alpha-pinene, (-)-beta-pinene and camphene. Primary deuterium isotope effects suggest that (-)-alpha-pinene and (-)-beta-pinene derive from alternative deprotonation of a common enzymatic intermediate
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene
-
?
geranyl diphosphate
(-)-beta-pinene + diphosphate
-
-
products are (-)-camphene, (-)-alpha-pinene, (-)-beta-pinene, (-)-limonene and myrcene
-
?
geranyl diphosphate
beta-pinene + diphosphate
-
products are 77% alpha-pinene + 14.7% beta-pinene + 5.5 beta-phellandrene
-
?
geranyl diphosphate
beta-pinene + diphosphate
-
products are 90% alpha-pinene, 10% beta-pinene
-
?
geranyl diphosphate
beta-pinene + diphosphate
-
stereochemistry of the product is not specified in the publication, reaction of recombinantly expressed S-limonene sythase mutant N345A/L423A/S454A enzyme lacking the N-terminal transit peptide
-
-
?
geranyl diphosphate
beta-pinene + diphosphate
-
-
-
?
geranyl diphosphate
beta-pinene + diphosphate
stereochemistry of the product is not specified in the publication
-
-
?
additional information
?
-
entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate
-
-
?
additional information
?
-
-
product profiles of mutant enzymes, overview
-
-
?
additional information
?
-
-
bicyclic products pinene and camphene are derived via the cyclization of the bound, tertiary intermediate (3R)-linalyl diphosphate. Limonene is formed via conformational foldings in addition to the cisoid,anti-endo-pattern. In the case of geranyl diphosphate, a preassociation mechanism is suggested in which optimum folding of the terpenyl chain precedes the initial ionization step
-
-
?
additional information
?
-
-
each product exhibits the same absolute configuration at the center derived from C-6 of geranyl diphosphate, i e. the isopropylidene-substituted carbon
-
-
?
additional information
?
-
-
enzymes removes the C4-proS-hydrogen of the substrate, the C3 proton of the corresponding pinyl cation, with a stereoselectivity exceeding 78% in the formation of (-)-alpha-pinene
-
-
?
additional information
?
-
-
product distribution varies with deuterium substitution at C4 and C10 of substrate. Kinetic isotope effects strongly indicate multiple bicyclic olefin production through the partitioning of common carbocation intermediates
-
-
?
additional information
?
-
-
substrates geranyl, neryl, and (3S)-linalyl diphosphate yield exclusively the (-)-isomer series, whereas (3R)-linalyl diphosphate affords the (+)-isomers at low rates
-
-
?
additional information
?
-
enzyme AvTPS1 (AvPS or pinene synthase) catalyzes GPP to form alpha-pinene and beta-pinene, the enzyme produces 63% beta-pinene as the major product
-
-
?
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C372S
replacement with corresponding residue of (-)-camphene synthase, 97% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene, while the levels of total pinenes remains relatively constant
C372S/C480S
replacement with corresponding residue of (-)-camphene synthase, 72% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
C372S/F597W
replacement with corresponding residue of (-)-camphene synthase, 100% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
C372S/F597W/S485C/F597W
replacement with corresponding residue of (-)-camphene synthase, 99% of wild-type activity. Mutant produces about 80%(-)-alpha-pinene and 10% (-)-beta-pinene
C372S/S485C
replacement with corresponding residue of (-)-camphene synthase, 92% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
C480S
replacement with corresponding residue of (-)-camphene synthase, 97% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene, while the levels of total pinenes remains relatively constant
C480S/F597W
replacement with corresponding residue of (-)-camphene synthase, 7% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
C480S/S485C
replacement with corresponding residue of (-)-camphene synthase, 70% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
F597W
replacement with corresponding residue of (-)-camphene synthase, 73% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene, while the levels of total pinenes remains relatively constant
S485C
replacement with corresponding residue of (-)-camphene synthase, 100% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene, while the levels of total pinenes remains relatively constant
S485C/F597W
replacement with corresponding residue of (-)-camphene synthase, 68% of wild-type activity. Mutant produces an increased proportion of (-)-alpha-pinene and a correspondingly decreased proportion of (-)-beta-pinene
H579A
-
site-directed mutagenesis, the mutant produces only 56.3% S-limonene
L423A/S454A
-
site-directed mutagenesis, mutation M2, the mutant shows altered substrate specificity and product profile compared to the wild-type enzyme
M458A
-
site-directed mutagenesis, the mutant produces only 3.2% S-limonene
N345A/L423A/S454A
-
site-directed mutagenesis, mutation M3 enlarges the active site, the mutant shows altered substrate specificity and product profile compared to the wild-type enzyme, the mutant acts as a pinene synthase and produces about 70% pinenes and has about 2fold increase in the yield of overall terpene products
N345A/L423A/S454G
-
site-directed mutagenesis, mutation M5, the mutant shows altered substrate specificity and product profile compared to the wild-type enzyme, products of M5 are composed of 9.8% alpha-pinene, 52.7% beta-pinene and 13.4% limonene, it has about 2fold increase in the yield of overall terpene products
N345G/L423A/S454A
-
site-directed mutagenesis, mutation M4, the mutant shows altered substrate specificity and product profile compared to the wild-type enzyme, products of M4 are composed of 18.81% alpha-pinene, 44.00% beta-pinene, and 16.2% limonene
S454G
-
site-directed mutagenesis, the mutation enlarges the active site, the mutant shows altered substrate specificity and product profile compared to the wild-type enzyme, the mutant enzyme produces about 46% alpha- and beta-pinenes and only about 52% limonene
T349A
-
site-directed mutagenesis, the mutant produces only 60.3% limonene
W324A
-
site-directed mutagenesis, the mutant produces only 18.1% S-limonene
N345A
-
site-directed mutagenesis, the mutant produces only 20.9%imonene
N345A
-
site-directed mutagenesis, the mutation enlarges the active site, the mutant shows altered substrate specificity and product profilecompared to the wild-type enzyme
S454A
-
site-directed mutagenesis, the mutant produces only 73.7% S-limonene
S454A
-
site-directed mutagenesis, the mutation enlarges the active site, the mutant shows altered substrate specificity and product profile compared to the wild-type enzyme
additional information
replacement of selected amino acid residues in (-)-pinene synthase with the corresponding residues from (-)-camphene synthase in an effort to identify the amino acids responsible for the catalytic diVerences. The approach produces an enzyme in which more than half of the product is channeled through an alternative pathway. Several (-)-pinene synthase to (-)-camphene synthase amino acid substitutions are necessary before catalysis is significantly altered
additional information
-
S-limonene synthase is converted to pinene or phellandrene synthases by site-directed mutagenesis, product profiles of mutant enzymes, overview
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Monoterpene synthases from grand fir (Abies grandis): cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4S)-limonene synthase, and (-)-(1S,5S)-pinene synthase
J. Biol. Chem.
272
21784-21792
1997
Abies grandis (O24475), Abies grandis
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Gijzen, M.; Lewinsohn, E.; Croteau, R
Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis)
Arch. Biochem. Biophys.
289
267-273
1991
Abies grandis
brenda
Wagschal, K.C.; Pyun H.J.; Coates, R.M.; Croteau, R.
Monoterpene biosynthesis: Isotope effects associates with bicyclic olefin formation catalyzed by pinene synthases from sage (Salvia officinalis)
Arch. Biochem. Biophys.
308
477-487
1994
Salvia officinalis
brenda
Croteau, R.; Wheeler, C.J.
Isotopically sensitive branching in the formation of cyclic monoterpenes: Proof that (-)-alpha-pinene and (-)-beta-pinene are synthesized by the same monoterpene cyclase via deprotonation of a common intermediate
Biochemistry
26
5383-5389
1987
Salvia officinalis
brenda
Croteau, R.; Satterwhite, D.M.; Cane, D.E.; Chang, C.C.
Biosynthesis of monoterpenes: Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophospahte to (+)- and (-) pinene and (+)- and (-)-camphene
J. Biol. Chem.
263
10063-10071
1988
Salvia officinalis
brenda
Croteau, R.; Satterwhite, D.M.
Biosynthesis of monoterpenes: Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage
J. Biol. Chem.
264
15309-15315
1989
Salvia officinalis
brenda
Lewinsohn, E.; Gijzen, M.; Croteau, R.
Wound-inducible pinene cyclase from grand fir: Purification, characterization, and renaturation after SDS-PAGE
Arch. Biochem. Biophys.
293
167-173
1992
Abies grandis
brenda
Pyun, H.J.; Wagschal, K.C.; Jung, D.; Coates, R.M.; Croteau, R.
Stereochemistry of the proton elimination in the formation of (+)- and (-)-alpha-pinene by monoterpene cyclases from sage (Salvia officinalis)
Arch. Biochem. Biophys.
308
488-496
1994
Salvia officinalis
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Lucker, J.; El Tamer, M.K.; Schwab, W.; Verstappen, F.W.; van der Plas, L.H.; Bouwmeester, H.J.; Verhoeven, H.A.
Monoterpene biosynthesis in lemon (Citrus limon). cDNA isolation and functional analysis of four monoterpene synthases
Eur. J. Biochem.
269
3160-3171
2000
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Cloning and functional characterization of a beta-pinene synthase from Artemisia annua that shows a circadian pattern of expression
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130
477-486
2002
Artemisia annua (Q94G53)
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Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from Abies grandis
Arch. Biochem. Biophys.
439
222-233
2005
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Arch. Biochem. Biophys.
320
257-265
1995
Pinus contorta
brenda
Bohlmann, J.; Phillips, M.; Ramachandiran, V.; Katoh, S.; Croteau, R.
cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis)
Arch. Biochem. Biophys.
368
232-243
1999
Abies grandis (Q9M7D0)
brenda
Phillips, M.; Savage, T.; Croteau, R.
Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers
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372
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Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration
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96
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73
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An integrative volatile terpenoid profiling and transcriptomics analysis for gene mining and functional characterization of AvBPPS and AvPS involved in the monoterpenoid biosynthesis in Amomum villosum
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9
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brenda
Xu, J.; Ai, Y.; Wang, J.; Xu, J.; Zhang, Y.; Yang, D.
Converting S-limonene synthase to pinene or phellandrene synthases reveals the plasticity of the active site
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137
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Mentha spicata
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