4.2.3.122: (+)-beta-pinene synthase
This is an abbreviated version!
For detailed information about (+)-beta-pinene synthase, go to the full flat file.
Reaction
Synonyms
(+)-pinene cyclase, AvPS, AvTPS1, cyclase III, More, pinene synthase, TPS1
ECTree
4.2.3.122 (+)-beta-pinene synthaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.2.3.122 - (+)-beta-pinene 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
(RS)-alpha-terpinyl diphosphate
limonene + diphosphate
-
-
about 90% limonene, 10% terpinolene. Enzyme is unable to discriminate between enantiomers of alpha-terpinyl diphosphate
-
?
linalyl diphosphate
myrcene + diphosphate
-
-
products are disproportionately high levels of acyclic olefins myrcene and ocimene and monocyclic olefins limonene and terpinolene. Limonene is formed via conformational foldings in addition to the cisoid, anti-endo-pattern
-
?
neryl diphosphate
myrcene + diphosphate
-
-
products are disproportionately high levels of acyclic olefins myrcene and ocimene and monocyclic olefins limonene and terpinolene. Limonene is formed via conformational foldings in addition to the cisoid, anti-endo-pattern
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
products are (+)-alpha-pinene, (+)-camphene, and lesser amounts of (+)-limonene, myrcene, and terpinolene. The bicyclic products of pinene and camphene are derived via the cyclization of the cisoid, anti-endo-conformers of the bound, tertiary allylic intermediate (3R)-linalyl diphosphate. A preassociation mechanism of geranyl diphosphate is suggested in which optimum folding of the terpenyl chain precedes the initial ionization step
-
?
geranyl diphosphate
(+)-alpha-pinene + diphosphate
-
-
reaction proceeds via (3R)-linalyl diphosphate and the (4R)-alpha-terpinyl cation. Products are (+)-alpha-pinene, and lesser amounts of related olefins
-
?
geranyl diphosphate
(+)-beta-pinene + diphosphate
-
-
36% (+)-alpha-pinene, 45% (+)beta-pinene
-
?
geranyl diphosphate
(+)-beta-pinene + diphosphate
-
-
products are (+)-alpha-pinene and (+)-beta-pinene
-
?
geranyl diphosphate
beta-pinene + diphosphate
-
stereochemistry is not specified in the publication, reaction of recombinantly expressed S-limonene sythase mutant N345A/L423A/S454A enzyme lacking the N-terminal transit peptide
-
-
?
additional information
?
-
-
product profiles of mutant enzymes, overview
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
enzyme AvTPS1 (AvPS or pinene synthase) catalyzes GPP to form alpha-pinene and beta-pinene, the enzyme produces 63% beta-pinene as the major product
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-
?
