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
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General Information
General Information on EC 4.2.3.108 - 1,8-cineole synthase
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evolution
metabolism
physiological function
additional information
enzyme AaTPS6 belongs to the terpene synthases family, TPS-b subfamily
evolution
the amounts and ratios of alpha-terpineol enantiomers is species-specific for cineole synthases and terpineol synthases of different species, overview. For Nicotinana forgetiana, the S:R ratio ((S)-(-)-alpha-terpineol to (R)-(+)-alpha-terpineol) is 7.7-7.9:1
evolution
the monoterpene synthase belongs to the terpene synthases superfamily, TPS-b clade
cyclization reactions of monoterpene synthases, overview. 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 synthesis of the acyclic beta-myrcene might proceed via the geranyl cation or via the linalyl cation by deprotonation. The intermediate alpha-terpinyl cation is the precursor for all cyclic monoterpenes. The 2,7-ring closure results in the pinyl cation, which is deprotonated to synthesize beta-pinene and alpha-pinene. Sabinene, with a cyclopropane ring, is released after two carbocation formations and 2,6-ring closure. alpha-Terpineol is formed after water capture of the alpha-terpinyl cation. Broken lines indicate possible reactions leading to 1,8-cineole. A cyclization reaction resulting in 1,8-cineole uses alpha-terpineol as a precursor. Enzyme structure homology modelling
metabolism
cyclization reactions of monoterpene synthases, overview. 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 synthesis of the acyclic beta-myrcene might proceed via the geranyl cation or via the linalyl cation by deprotonation. The intermediate alpha-terpinyl cation is the precursor for all cyclic monoterpenes. The 2,7-ring closure results in the pinyl cation, which is deprotonated to synthesize beta-pinene and alpha-pinene. Sabinene, with a cyclopropane ring, is released after two carbocation formations and 2,6-ring closure. alpha-Terpineol is formed after water capture of the alpha-terpinyl cation. Broken lines indicate possible reactions leading to 1,8-cineole. A cyclization reaction resulting in 1,8-cineole uses alpha-terpineol as a precursor. Enzyme structure homology modelling
metabolism
in Artemisia annua, three monoterpene synthases AaTPS2, AaTPS5, and AaTPS6, produce beta-myrcene, camphene, and 1,8-cineole as the major products, respectively
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. The 1,8-cineole content is also higher in femal flowers, overview
physiological function
the monoterpene synthase TPS6 might play a role in plant-environment interactions
the amino acids at positions 147, 148, and 266 determine the different terpineol-cineole ratios in Nicotiana suaveolens cineole synthase and Nicotiana langsdorffii terpineol synthase
additional information
the amino acids at positions 147, 148, and 266 determine the different terpineol-cineole ratios in Nicotiana suaveolens cineole synthase and Nicotiana langsdorffii terpineol synthase. Homology modeling of 1,8-cineole synthases of Nicotiana forgetiana and Nicotiana suaveolens