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Information on EC 4.2.3.108 - 1,8-cineole synthase
for references in articles please use BRENDA:EC4.2.3.108
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IUBMB Comments
Requires Mn2+ or Zn2+. Mg2+ is less effective than either. 1,8-Cineole is the main product from the enzyme with just traces of other monoterpenoids. The oxygen atom is derived from water. The reaction proceeds via linalyl diphosphate and α-terpineol, the stereochemistry of both depends on the organism. However neither intermediate can substitute for geranyl diphosphate. The reaction in Salvia officinalis (sage) proceeds via (–)-(3R)-linalyl diphosphate [1-3] while that in Arabidopsis (rock cress) proceeds via (+)-(3S)-linalyl diphosphate .
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
- 4.2.3.108
-
monoterpene
- synthases
-
terpene
- salvia
- officinalis
-
+-bornyl
- sabinene
- sage
- lamiaceae
- trichome
- eucalyptus
- camphor
-
multi-product
-
spasmolytic
-
hoffmanns
-
astringent
- lavandula
- caryophyllene
-
linalyl
- beta-pinene
- gpp
-
carbocation
- lavender
- hypoxylon
- terpinolene
-
alpha-terpineole
showSynonyms
1,8-cineole synthase, aatps6, 1,8-cineole cyclase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1,8-cineole cyclase
-
-
-
-
1,8-cineole synthetase
-
-
-
-
CIN
geranyl pyrophoshate:1,8-cineole cyclase
-
-
-
-
SCLAV_p0982
SSCG_00536
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + H2O = 1,8-cineole + diphosphate
-
-
-
-
geranyl diphosphate + H2O = 1,8-cineole + diphosphate
substrate in left-hynded screw-sense orientation isomerizes to (3R)-linalyl diphosphate which in anti,endo-conformation cyclizes to the (4R)-alpha-terpinyl intermediate and thence to cineole following the addition of water
geranyl diphosphate + H2O = 1,8-cineole + diphosphate
syn-stereochemistry for both C-O-bond-forming steps. Reaction starts with allylic rearrangement of geranyl diphosphate to (R)-linalyl diphosphate, followed by SN' cyclization to alpha-terpineol and proton-induced cyclization of the C=C-double bond and the tertiary hydroxyl groups
geranyl diphosphate + H2O = 1,8-cineole + diphosphate
proposed mechanism for the formation of 1,8-cineole, the reaction can proceed via (R)-alpha-terpinyl cation and (R)-alpha-terpineol, as well as via (S)-alpha-terpinyl cation and (S)-alpha-terpineol, the catalytic dyad is formed by H502 and E249. Depending on the stereochemistry of the intermediate, the protonation of the double bond of the alpha-terpinyl cation is provided by a proton relay via the hydroxyl groups of either Tyr496 or Thr278. The substrate GPP is ionized by diphosphate elimination, resulting in the geranyl cation. Subsequently, this cation is converted into the linalyl cation and alpha-terpinyl cation. The intermediate alpha-terpinyl cation is the precursor for all cyclic monoterpenes. 1,8-Cineol is possibly directly formed from geranyl diphosphate, and a cyclization reaction resulting in 1,8-cineole uses alpha-terpineol as a precursor. alpha-Terpineol is formed after water capture of the alpha-terpinyl cation
geranyl diphosphate + H2O = 1,8-cineole + diphosphate
the substrate GPP is ionized by diphosphate elimination, resulting in the geranyl cation. Subsequently, this cation is converted into the linalyl cation and alpha-terpinyl cation. The intermediate alpha-terpinyl cation is the precursor for all cyclic monoterpenes. 1,8-Cineol is possibly directly formed from geranyl diphosphate, and a cyclization reaction resulting in 1,8-cineole uses alpha-terpineol as a precursor. alpha-Terpineol is formed after water capture of the alpha-terpinyl cation. Proposed mechanism for the formation of 1,8-cineole
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PATHWAY SOURCE
PATHWAYS
MetaCyc
monoterpene biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase (cyclizing, 1,8-cineole-forming)
Requires Mn2+ or Zn2+. Mg2+ is less effective than either. 1,8-Cineole is the main product from the enzyme with just traces of other monoterpenoids. The oxygen atom is derived from water. The reaction proceeds via linalyl diphosphate and alpha-terpineol, the stereochemistry of both depends on the organism. However neither intermediate can substitute for geranyl diphosphate. The reaction in Salvia officinalis (sage) proceeds via (-)-(3R)-linalyl diphosphate [1-3] while that in Arabidopsis (rock cress) proceeds via (+)-(3S)-linalyl diphosphate [4].
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CAS REGISTRY NUMBER
COMMENTARY
110637-19-9
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(3R)-linalyl diphosphate + H2O
? + diphosphate
Substrates: -
Products: -
Products: -
?
(3S)-linalyl diphosphate + H2O
? + diphosphate
Substrates: -
Products: -
Products: -
?
neryl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: 61% 1,8-cineole plus 18.5% sabinene, 8% alpha-phellandrene, 3.3% limonene, and 5.5% alpha-terpineol
Products: 61% 1,8-cineole plus 18.5% sabinene, 8% alpha-phellandrene, 3.3% limonene, and 5.5% alpha-terpineol
?
neryl diphosphate + H2O
? + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
1,8-cineole + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: 52% 1,8-cineole plus 0.6% (+)-alpha-thujene, 1.9% (2)-(1S)-alpha-pinene, 14.5% (-)-sabinene, 7.8% (2)-(1S)-beta-pinene, 13.3% myrcene, 4.0% (2)-(4S)-limonene, (E)-2.7% beta-ocimene, 0.8% terpinolene, and 2.4% alpha-terpineol
Products: 52% 1,8-cineole plus 0.6% (+)-alpha-thujene, 1.9% (2)-(1S)-alpha-pinene, 14.5% (-)-sabinene, 7.8% (2)-(1S)-beta-pinene, 13.3% myrcene, 4.0% (2)-(4S)-limonene, (E)-2.7% beta-ocimene, 0.8% terpinolene, and 2.4% alpha-terpineol
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: 80% 1,8-cineole plus 7.9% sabinene, 6.6% alpha-phellandrene, 2.3% limonene, and 1.7% alpha-terpineol
Products: 80% 1,8-cineole plus 7.9% sabinene, 6.6% alpha-phellandrene, 2.3% limonene, and 1.7% alpha-terpineol
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: products are sabinene, beta-myrcene, limonene, 1,8-cineole, and 41% alpha-terpineol
Products: products are sabinene, beta-myrcene, limonene, 1,8-cineole, and 41% alpha-terpineol
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: products are alpha-pinene, beta-pinene, sabinene, beta-myrcene, limonene, 1,8-cineole and alpha-terpineol. 1,8-Cineole and alpha-terpineol are the major products, enzyme synthesizes 2- to 3fold more cineol than alpha-terpineol
Products: products are alpha-pinene, beta-pinene, sabinene, beta-myrcene, limonene, 1,8-cineole and alpha-terpineol. 1,8-Cineole and alpha-terpineol are the major products, enzyme synthesizes 2- to 3fold more cineol than alpha-terpineol
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: products are alpha-pinene, beta-pinene, sabinene, beta-myrcene, limonene, 1,8-cineole and alpha-terpineol. 1,8-Cineole and alpha-terpineol are the major products, enzyme synthesizes 2- to 3fold more cineol than alpha-terpineol
Products: products are alpha-pinene, beta-pinene, sabinene, beta-myrcene, limonene, 1,8-cineole and alpha-terpineol. 1,8-Cineole and alpha-terpineol are the major products, enzyme synthesizes 2- to 3fold more cineol than alpha-terpineol
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: the enzyme releases alpha-terpineol as the main compound as a terpineol synthase (TER). The S to R ratio is 7.9:1 and 7.7:1 in two experimental passages
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: products are sabinene, beta-myrcene, limonene, 1,8-cineole, and 36% alpha-terpineol
Products: products are sabinene, beta-myrcene, limonene, 1,8-cineole, and 36% alpha-terpineol
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: products are alpha-pinene, beta-pinene, sabinene, beta-myrcene, limonene, 1,8-cineole and alpha-terpineol. 1,8-Cineole and alpha-terpineol are the major products, enzyme synthesizes 2- to 3fold more cineol than alpha-terpineol
Products: products are alpha-pinene, beta-pinene, sabinene, beta-myrcene, limonene, 1,8-cineole and alpha-terpineol. 1,8-Cineole and alpha-terpineol are the major products, enzyme synthesizes 2- to 3fold more cineol than alpha-terpineol
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: products are alpha-pinene, beta-pinene, sabinene, beta-myrcene, limonene, 1,8-cineole and alpha-terpineol. 1,8-cineole is the major compound comprising ca. 50% of the products. alpha-Terpineol contributes approximately 25%
Products: products are alpha-pinene, beta-pinene, sabinene, beta-myrcene, limonene, 1,8-cineole and alpha-terpineol. 1,8-cineole is the major compound comprising ca. 50% of the products. alpha-Terpineol contributes approximately 25%
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: major product is 1,8-cineole plus limonene, sabinene, E-beta-ocimene, b-myrcene, alpha-pinene, and alpha-terpineole
Products: major product is 1,8-cineole plus limonene, sabinene, E-beta-ocimene, b-myrcene, alpha-pinene, and alpha-terpineole
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: the enzyme releases alpha-terpineol as the main compound as a terpineol synthase (TER). The S to R ratio is 6.6:1 and 6.5:1 in two experimental passages
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: 72.4% 1,8-cineole, 7.1% alpha-terpineol, 9.1% beta-pinene, 4.6% alpha-pinene, 3.6% sabinene, 2.2% myrcene, and <1% limonene
Products: 72.4% 1,8-cineole, 7.1% alpha-terpineol, 9.1% beta-pinene, 4.6% alpha-pinene, 3.6% sabinene, 2.2% myrcene, and <1% limonene
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: 79% 1,8-cineole plus 20% of a mixture of (+)- and (-)-alpha-pinene, (+)- and (-)-beta-pinene, myrcene and (+)-sabinene
Products: 79% 1,8-cineole plus 20% of a mixture of (+)- and (-)-alpha-pinene, (+)- and (-)-beta-pinene, myrcene and (+)-sabinene
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: water is the sole source of the ether oxygen atom of 1,8-cineole
Products: water is the sole source of the ether oxygen atom of 1,8-cineole
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: 1,8-cineole is the single major product
Products: 1,8-cineole is the single major product
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: 1,8-cineole is the single major product
Products: 1,8-cineole is the single major product
?
additional information
?
-
Substrates: no substrate: farnesyl diphosphate
Products: -
Products: -
?
additional information
?
-
Substrates: no substrate: farnesyl diphosphate
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme AaTPS6 produces multiple products with 1,8-cineole as major product (59.28% of total),in addition to ten other products including sabinene and beta-phellandrene (together 19.04%), alpha-terpineol (7.84%), trans-sabinene hydrate(4.03%), (-)-alpha-pinene (3.00%), cis-beta-terpineol (2.51%), beta-myrcene (2.01%), alpha-thujene (0.69%), as well as two unidentified minor products. No activity with farnesyl diphosphate or geranylgeranyl diphosphate
Products: -
Products: -
?
additional information
?
-
-
Substrates: enzyme AaTPS6 produces multiple products with 1,8-cineole as major product (59.28% of total),in addition to ten other products including sabinene and beta-phellandrene (together 19.04%), alpha-terpineol (7.84%), trans-sabinene hydrate(4.03%), (-)-alpha-pinene (3.00%), cis-beta-terpineol (2.51%), beta-myrcene (2.01%), alpha-thujene (0.69%), as well as two unidentified minor products. No activity with farnesyl diphosphate or geranylgeranyl diphosphate
Products: -
Products: -
?
additional information
?
-
-
Substrates: no substrate: farnesyl diphosphate
Products: -
Products: -
?
additional information
?
-
Substrates: with geranyl pyrophosphate (GPP) as a substrate, LnTPS1 catalyzes the formation of mostly 1,8-cineole, with alpha-thujene, alpha-pinene, beta-pinene, alpha-terpinene, gamma-terpinene, alpha-terpinolene, and a few other monoterpenes also produced, as detected by GC-MS analysis
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme is a multi product enzyme synthesizing simultaneously the seven monoterpenes of the cineole cassette
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme is a multi product enzyme synthesizing simultaneously the seven monoterpenes of the cineole cassette
Products: -
Products: -
?
additional information
?
-
Substrates: the formation of alpha-terpineol starts by a nucleophilic attack of water. During this attack, the alpha-terpinyl cation is stabilized by Pi-stacking with a tryptophan side chain (Tryp253). The hypothesized catalytic mechanism of alpha-terpineol-to-1,8-cineole conversion is initiated by a catalytic dyad (His502 and Glu249), acting as a base, and a threonine (Thr278) providing the subsequent rearrangement from terpineol to cineol by catalyzing the autoprotonation of (2S)-2-alpha-terpineol, which is the favored enantiomer product of the recombinant enzymes. Product analysis and quantification by GC-MS. Binding structure of the reactive intermediate alpha-terpinyl cation in the active site of cineole synthase involving residues Trp253, His502, and Thr278, overview. The hydroxyl group of Tyr496 is necessary to control the orientation of Asn419. This Asn itself is proposed to be involved in binding and fixation of the diphosphate moiety of the substrate. Major role of Thr278 in the formation of cineole by fixing the intermediate alpha-terpineol and supporting the autoprotonation of its double bond. Residue Phe266 is relevant for the product outcome of the 1,8-cineole synthase
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme is a multi product enzyme synthesizing simultaneously the seven monoterpenes of the cineole cassette
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme is a multi product enzyme synthesizing simultaneously the seven monoterpenes of the cineole cassette
Products: -
Products: -
?
additional information
?
-
Substrates: the formation of alpha-terpineol strats by a nucleophilic attack of water. During this attack, the alpha-terpinyl cation is stabilized by Pi-stacking with a tryptophan side chain (Tryp253). The hypothesized catalytic mechanism of alpha-terpineol-to-1,8-cineole conversion is initiated by a catalytic dyad (His502 and Glu249), acting as a base, and a threonine (Thr278) providing the subsequent rearrangement from terpineol to cineol by catalyzing the autoprotonation of (2S)-2-alpha-terpineol, which is the favored enantiomer product of the recombinant enzymes. Product analysis and quantification by GC-MS
Products: -
Products: -
?
additional information
?
-
Substrates: no substrate: farnesyl diphosphate
Products: -
Products: -
?
additional information
?
-
Substrates: no substrate: farnesyl diphosphate
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
Substrates: -
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
additional information
additional information
the enzyme depends on the presence of divalent cations, Mg2+ is the preferred metal ion
additional information
-
the enzyme depends on the presence of divalent cations, Mg2+ is the preferred metal ion
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-hydroxymercuribenzoate
inhibition is reversed by presence of cysteine
diethyl dicarbonate
inhibition is reversed by presence of hydroxylamine
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
enzyme activity reaches its maximum at the second day after anthesis when flowers are fully opened. Enzyme activity is highest at the transition from day to night, diurnal rhythm
-
additional information
enzyme activity reaches its maximum at the second day after anthesis when flowers are fully opened. Enzyme activity is highest at the transition from day to night, diurnal rhythm
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00004
geranyl diphosphate
recombinant mutant F266T, pH and temperature not specified in the publication
0.00004
geranyl diphosphate
recombinant mutant F266V, pH and temperature not specified in the publication
0.00012
geranyl diphosphate
recombinant mutant F266S, pH and temperature not specified in the publication
0.00019
geranyl diphosphate
recombinant wild-type enzyme, pH and temperature not specified in the publication
0.0002
geranyl diphosphate
temperature not specified in the publication, pH not specified in the publication
0.0129
geranyl diphosphate
mutant N338I/A339T/G447S/I449P/P450T, pH 7.0, 22°C
additional information
additional information
Michaelis-Menten kinetics
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000058
geranyl diphosphate
recombinant mutant F266T, pH and temperature not specified in the publication
0.00008
geranyl diphosphate
recombinant mutant F266V, pH and temperature not specified in the publication
0.00029
geranyl diphosphate
recombinant mutant F266S, pH and temperature not specified in the publication
0.00041
geranyl diphosphate
recombinant wild-type enzyme, pH and temperature not specified in the publication
0.001
geranyl diphosphate
temperature not specified in the publication, pH not specified in the publication
0.0043
geranyl diphosphate
mutant N338I/A339T/G447S/I449P/P450T, pH 7.0, 22°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.33
geranyl diphosphate
mutant N338I/A339T/G447S/I449P/P450T, pH 7.0, 22°C
1.45
geranyl diphosphate
recombinant mutant F266T, pH and temperature not specified in the publication
2
geranyl diphosphate
recombinant mutant F266V, pH and temperature not specified in the publication
2.157
geranyl diphosphate
recombinant wild-type enzyme, pH and temperature not specified in the publication
2.416
geranyl diphosphate
recombinant mutant F266S, pH and temperature not specified in the publication
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25 - 45
the recombinant enzyme AaTPS6 activity does not differ greatly at the range from 25°C to 40°C, it reaches peak at 25°C, has its maximal activity at 40°C, and retains 70% at 45°C, activity drops sharply above 40°C
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
parents Lavandula angustifolia and Lavandula latifolia
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
promoter activity is primarily found in the epidermis, cortex, and stele of mature primary and lateral roots, but not in the root meristem or the elongation zone
brenda
additional information
promoter activity is primarily found in the epidermis, cortex, and stele of mature primary and lateral roots, but not in the root meristem or the elongation zone
brenda
high enzyme content, fresh Laurus nobilis leaves, the monoterpene 1,8-cineole is the main volatile compound, and alpha-terpinyl acetate, terpinene-4-ol, alpha- and beta-pinene, sabinene, and linalool are reported to occur in appreciable levels
brenda
-
gene expression of monoterpene synthases and actual monoterpene formation is highest in young leaf
brenda
sabinene synthase transcripts show the highest monoterpene synthase transcript expression, about an order of magnitude higher than cineole synthase and borneol synthase
brenda
adaxial and abaxial epidermis of petals. 1,8-cineole is the major compound emitted
brenda
promoter activity is primarily found in the epidermis, cortex, and stele of mature primary and lateral roots, but not in the root meristem or the elongation zone
brenda