4.2.3.116: (+)-camphene synthase
This is an abbreviated version!
For detailed information about (+)-camphene synthase, go to the full flat file.
Reaction
Synonyms
AaTPS5, cyclase I, More
ECTree
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Substrates Products
Substrates Products on EC 4.2.3.116 - (+)-camphene synthase
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REACTION DIAGRAM
(3R)-linalyl diphosphate
(+)-camphene + diphosphate
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(3R)-enantiomer is preferred over (3S)-enantiomer
products are (+)-camphene and (+)alpha-pinene
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?
(3S)-linalyl diphosphate
(-)-camphene + diphosphate
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(3R)-enantiomer is preferred over (3S)-enantiomer
products are (-)-camphene and (-)alpha-pinene
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?
geranyl diphosphate
camphene + diphosphate
stereochemistry is not specified in the publication
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-
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neryl diphosphate
(+)-camphene + diphosphate
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products are (+)-camphene and (+)alpha-pinene
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(+)-camphene + diphosphate
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products are 39% (+)-limonene, 22% terpinolene, 16% (+)-camphene, 14% (+)-alpha-pinene, 8% beta-myrcene, 1% alpha-phellandrene. Product pattern changes markedly to 46% limonene, 9% terpinolene, 23% alpha-pinene, 5% beta-myrcene and 4% alpha-phellandrene, when Mn2+ is supplied instead of Mg2+
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geranyl diphosphate
(+)-camphene + diphosphate
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31% (+)-alpha-pinene, 29% (+)-camphene
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geranyl diphosphate
(+)-camphene + diphosphate
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products are (+)-alpha-pinene and (+)-camphene
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geranyl diphosphate
(+)-camphene + diphosphate
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products are (+)-camphene and (+)alpha-pinene
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?
geranyl diphosphate
(+)-camphene + diphosphate
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products are (+)-camphene, (+)-alpha-pinene and (+)-limonene
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geranyl diphosphate
(+)-camphene + diphosphate
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products are 25% (+)-alpha-pinene, 25% (+)-camphene, 43% (+)-limonene, and 7% myrcene. Reaction in organic solvent gives the same olefin distribution as in aqueous buffer
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GC-MS analysis and identification of products from enzyme catalysis, overview. Enzyme AaTPS5 catalyzes the production of five monoterpenes, of which camphene is the major one which accounts for 52.12% of the total, and (-)-alpha-pinene (30.08%), (-)-beta-pinene (3.89%), tricyclene (2.68%), and beta-myrcene (1.23%) are the less abundant products
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additional information
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GC-MS analysis and identification of products from enzyme catalysis, overview. Enzyme AaTPS5 catalyzes the production of five monoterpenes, of which camphene is the major one which accounts for 52.12% of the total, and (-)-alpha-pinene (30.08%), (-)-beta-pinene (3.89%), tricyclene (2.68%), and beta-myrcene (1.23%) are the less abundant products
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additional information
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no substrate: farnesyl diphosphate, geranylgeranyl diphosphate
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additional information
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enzyme removes the C4-proR-hydrogen of the substrate, the C3 proton trans to the dimethyl bridge of the pinyl nucleus, with a stereoselectivity exceeding 94% in the formation of (+)-alpha-pinene
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additional information
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product distribution varies with deuterium substitution at C4 and C10 of substrate. Kinetic isotope effects strongly indicate multiple bicyclic olefin production through the partitioning of common carbocation intermediates
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