4.2.3.108: 1,8-cineole synthase
This is an abbreviated version!
For detailed information about 1,8-cineole synthase, go to the full flat file.
Word Map on EC 4.2.3.108
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4.2.3.108
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monoterpene
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synthases
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terpene
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salvia
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officinalis
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+-bornyl
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sabinene
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sage
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lamiaceae
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trichome
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eucalyptus
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camphor
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multi-product
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spasmolytic
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hoffmanns
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astringent
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lavandula
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caryophyllene
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linalyl
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beta-pinene
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gpp
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carbocation
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lavender
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hypoxylon
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terpinolene
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alpha-terpineole
- 4.2.3.108
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monoterpene
- synthases
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terpene
- salvia
- officinalis
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+-bornyl
- sabinene
- sage
- lamiaceae
- trichome
- eucalyptus
- camphor
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multi-product
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spasmolytic
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hoffmanns
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astringent
- lavandula
- caryophyllene
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linalyl
- beta-pinene
- gpp
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carbocation
- lavender
- hypoxylon
- terpinolene
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alpha-terpineole
Reaction
Synonyms
1,8-cineole cyclase, 1,8-cineole synthetase, AaTPS6, CIN, CinS, geranyl pyrophoshate:1,8-cineole cyclase, leucoplast 1,8-cineole synthase, LnTPS1, plastid terpineol synthase, SabS1, SCLAV_p0982, SSCG_00536, SSS, TER, TPS1, TPS6
ECTree
4.2.3.108 1,8-cineole synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.2.3.108 - 1,8-cineole synthase
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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
neryl diphosphate + H2O
1,8-cineole + diphosphate
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61% 1,8-cineole plus 18.5% sabinene, 8% alpha-phellandrene, 3.3% limonene, and 5.5% alpha-terpineol
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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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
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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80% 1,8-cineole plus 7.9% sabinene, 6.6% alpha-phellandrene, 2.3% limonene, and 1.7% alpha-terpineol
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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products are sabinene, beta-myrcene, limonene, 1,8-cineole, and 41% alpha-terpineol
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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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
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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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
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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products are sabinene, beta-myrcene, limonene, 1,8-cineole, and 36% alpha-terpineol
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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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
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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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%
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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major product is 1,8-cineole plus limonene, sabinene, E-beta-ocimene, b-myrcene, alpha-pinene, and alpha-terpineole
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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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
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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79% 1,8-cineole plus 20% of a mixture of (+)- and (-)-alpha-pinene, (+)- and (-)-beta-pinene, myrcene and (+)-sabinene
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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water is the sole source of the ether oxygen atom of 1,8-cineole
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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1,8-cineole is the single major product
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?
geranyl diphosphate + H2O
1,8-cineole + diphosphate
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1,8-cineole is the single major product
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?
additional information
?
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no substrate: farnesyl diphosphate
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?
additional information
?
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no substrate: farnesyl diphosphate
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
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enzyme is a multi product enzyme synthesizing simultaneously the seven monoterpenes of the cineole cassette
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?
additional information
?
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enzyme is a multi product enzyme synthesizing simultaneously the seven monoterpenes of the cineole cassette
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?
additional information
?
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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
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?
additional information
?
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enzyme is a multi product enzyme synthesizing simultaneously the seven monoterpenes of the cineole cassette
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?
additional information
?
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enzyme is a multi product enzyme synthesizing simultaneously the seven monoterpenes of the cineole cassette
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-
?
additional information
?
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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
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?
additional information
?
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no substrate: farnesyl diphosphate
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?
additional information
?
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no substrate: farnesyl diphosphate
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?
