Information on EC 4.2.3.114 - gamma-terpinene synthase

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The expected taxonomic range for this enzyme is: Gunneridae

EC NUMBER
COMMENTARY
4.2.3.114
-
RECOMMENDED NAME
GeneOntology No.
gamma-terpinene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
geranyl diphosphate = gamma-terpinene + diphosphate
show the reaction diagram
major products sabinene and gamma-terpinene are formed by a cyclization mechanism involving a 1,2-hydride shift in the alpha-terpinyl cation intermediate
O81193
geranyl diphosphate = gamma-terpinene + diphosphate
show the reaction diagram
-
-
-
-
geranyl diphosphate = gamma-terpinene + diphosphate
show the reaction diagram
ionization of geranyl diphosphate folded in left-handed helical form gives, by syn-isomerization, (3R)-linalyl diphosphate, which by rotation about C2-C3 provides the cisoid, anti-endo conformation. Ionization and cyclization of this bound intermediate yield the (4R)-alpha-terpinyl cation that, following the 1,2-hydride shift, affords the terpinen-4-yl cation. Loss of the (5S)-proton terminates the reaction to generate gamma-terpinene
-
geranyl diphosphate = gamma-terpinene + diphosphate
show the reaction diagram
mechanism involves the cyclizazion of the acyclic precursor, loss of a proton from C5 to form the delta4 double bond, and a 1,2-hydride shift fom C4 to C8 to give gamma-terpinene
-
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase (cyclizing, gamma-terpinene-forming)
Isolated from Thymus vulgaris (thyme) [1,2], Citrus limon (lemon) [3], Citrus unshiu (satsuma) [4] and Origanum vulgare (oregano) [5]. Requires Mg2+. Mn2+ less effective. The reaction involves a 1,2-hydride shift. The 5-pro-S hydrogen of geranyl diphosphate is lost. Traces of several other monoterpenoids are formed in addition to gamma-terpinene.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
ClcTS
-
-
-
-
OvTPS2
-
-
-
-
RPS2
E2E2P0
-
CAS REGISTRY NUMBER
COMMENTARY
68943-55-5
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
six different variants of the gene are distinguishable according to sequence characteristics in intron 3, after comprehensive analysis in Origanum dubium, Origanum majorana, Origanum onites, and Origanum syriacum. The formation of characteristic essential oil compounds is associated with the presence of variants 1 and/or 3 and/or 4 in the gene. In plants lacking these variants, the compounds are completely absent or present in trace amounts only
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
gamma-terpinene + diphosphate
show the reaction diagram
-
-
-
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
show the reaction diagram
-
-
ionization of geranyl diphosphate folded in left-handed helical form gives, by syn-isomerization, (3R)-linalyl diphosphate, which by rotation about C2-C3 provides the cisoid, anti-endo conformation. Ionization and cyclization of this bound intermediate yield the (4R)-alpha-terpinyl cation that, following the 1,2-hydride shift, affords the terpinen-4-yl cation. Loss of the (5S)-proton terminates the reaction to generate gamma-terpinene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
show the reaction diagram
-, Q6F5H1
-
plus small amounts of alpha-pinene, limonene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
show the reaction diagram
Q8L5K4
-
products are 71.4% gamma-terpinene, with lower amounts of limonene (9.1%), alpha-pinene (5.6%), beta-pinene (4.7%), alpha-terpinolene (3.7%), alpha-thujene (2.5%), alpha-terpinene (1.7%), myrcene (0.9%), sabinene (0.4%) and a trace of p-cymene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
show the reaction diagram
E2E2P0
-
products are 80% gamma-terpinene and the minor products, alpha-thujene (7.2%), alpha-terpinene (6%), myrcene (2.6%), sabinene (1.3%), (+)-R-limonene (1.2%), alpha-pinene (1%) and alpha-phellandrene (0.8%), as well as trace amounts of p-cymene and beta-pinene
-
?
geranyl diphosphate
gamma-terpinene + diphosphate
show the reaction diagram
-
-
products are about 64% gamma-terpinen, 10% alpha-thujene, 4% myrcene, 4% alpha-terpinene, 2% limonene, 3% linalool, 2% terpinen-4-ol, 3% alpha-terpineol
-
?
geranyl diphosphate + H2O
gamma-terpinene + diphosphate
show the reaction diagram
O81193
-
63% sabinene, 21% gamma-terpinene, 7% terpinolene, 6.5% limonene, and 2.5% myrcene
-
?
neryl diphosphate
gamma-terpinene + diphosphate
show the reaction diagram
-
-
75% gamma-terpinene, 20% alpha-thujene, 5% alpha-terpineol, partially purified enzyme
-
?
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
Q8L5K4
or Mn2+, Mn2+ is preferred over Mg2+
Mg2+
-
or Mn2+, required, Mg2+ is preferred over Mn2+
Mg2+
-
or Mn2+, required. Optimum concentration 20 mM
Mg2+
E2E2P0
or Mn2+, required. Optimum concentration of Mg2+ 0.025 mM, 44% of the activity wit Mn2+
Mn2+
Q8L5K4
or Mg2+, Mn2+ is preferred over Mg2+, optimum concentration 0.6 mM
Mn2+
-
or Mg2+, required, about 60% of the efficiency qith Mg2+
Mn2+
-
or Mg2+, required. 50% of the efficiency with Mg2+
Mn2+
E2E2P0
or Mg2+, required. Mn2+ is preferred over Mg2+, optimum concentration 0.001 mM
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
4-hydroxymercuribenzoate
-
-
benzyl bromide
-
-
diethyl dicarbonate
-
-
diphosphate
-
-
EDTA
-
1 mM, complete inactivation
additional information
-
not inhibitory: gamma-terpinene, p-cymene, thymol
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0026
-
geranyl diphosphate
-
pH 6.8, 30C
0.0027
-
geranyl diphosphate
Q8L5K4
pH 7.0, 30C
0.0074
-
geranyl diphosphate
O81193
pH 7.1, 31C
0.00871
-
geranyl diphosphate
E2E2P0
pH 6.8, 30C
0.014
-
geranyl diphosphate
-
pH 6.6, 30C
0.009
-
neryl diphosphate
-
pH 6.6, 30C
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0035
-
4-hydroxymercuribenzoate
-
pH 6.8, 30C
2
-
benzyl bromide
-
pH 6.0, 30C
0.01
-
diethyl dicarbonate
-
pH 7.0, 30C
0.5
-
diphosphate
-
pH 6.8, 30C
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
149
-
-
pH 6.8, 30C
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.8
-
E2E2P0
-
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6
6.5
E2E2P0
half maximal activity
7.2
7.5
E2E2P0
half maximal activity
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
28
-
E2E2P0
-
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4.9
-
-
isoelectric focusing
5.2
-
O81193
calculated
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
Q8L5K4
glants of fruit lavedo and fruit peel
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
96000
-
-
gel filtraion
96000
-
-
gel fitlration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
O81193
x * 68490, calculated
dimer
-
2 * 55000, SDS-PAGE
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
addition of either 20% glycerol or 1 mM substrate does not significantly improve stability
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
0C, 40 mM sodium phosphate, 5 mM MgCl2, 0.5 mM dithioerythritol, loss of 60% of activity within 1 week
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli
Q8L5K4
expression in Escherichia coli
-, Q6F5H1
expression in Escherichia coli
O81193
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
terpene synthase expression levels directly control the composition of the essential oil
E2E2P0