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 hide
4.2.3.114
-
RECOMMENDED NAME
GeneOntology No.
gamma-terpinene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = gamma-terpinene + diphosphate
show the reaction diagram
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.
CAS REGISTRY NUMBER
COMMENTARY hide
68943-55-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
-
uniProt
Manually annotated by BRENDA team
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
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
gamma-terpinene + diphosphate
show the reaction diagram
geranyl diphosphate + H2O
gamma-terpinene + diphosphate
show the reaction diagram
-
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
-
?
additional information
?
-
no substrate farnesyl diphosphate
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
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]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0026 - 0.014
geranyl diphosphate
0.009
neryl diphosphate
-
pH 6.6, 30C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0035
4-hydroxymercuribenzoate
Thymus vulgaris
-
pH 6.8, 30C
2
benzyl bromide
Thymus vulgaris
-
pH 6.0, 30C
0.01
diethyl dicarbonate
Thymus vulgaris
-
pH 7.0, 30C
0.5
diphosphate
Thymus vulgaris
-
pH 6.8, 30C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
149
-
pH 6.8, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 6.5
half maximal activity
7.2 - 7.5
half maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.9
-
isoelectric focusing
5.2
calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
glants of fruit lavedo and fruit peel
Manually annotated by BRENDA team
high expression in shoot of in vitro plantlet
Manually annotated by BRENDA team
additional information
no expression in root
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 55000, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
homology modeling based on gamma-terpinene synthase from Origanum vulgare. Besides the aspartate-rich region DDxxD, the sites Asp452, Thr456 and Glu460 involved on stabilization of active site by Mg2+ cofactor are also conserved
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
addition of either 20% glycerol or 1 mM substrate does not significantly improve stability
-
STORAGE STABILITY
ORGANISM
UNIPROT
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
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
terpene synthase expression levels directly control the composition of the essential oil