4.2.3.52: (4S)-beta-phellandrene synthase (geranyl-diphosphate-cyclizing)
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For detailed information about (4S)-beta-phellandrene synthase (geranyl-diphosphate-cyclizing), go to the full flat file.
Word Map on EC 4.2.3.52
Reaction
Synonyms
(-)-(4S)-beta-phellandrene synthase, (-)-beta-phellandrene synthase, beta-phellandrene synthase, OPHLS, phellandrene synthase, PHLS
ECTree
4.2.3.52 (4S)-beta-phellandrene synthase (geranyl-diphosphate-cyclizing)Advanced search results
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results (Substrates Products
Substrates Products on EC 4.2.3.52 - (4S)-beta-phellandrene synthase (geranyl-diphosphate-cyclizing)
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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
geranyl diphosphate
beta-myrcene + beta-phellandrene + beta-pinene + alpha-phellandrene + diphosphate
-
-
-
?
geranyl diphosphate
beta-phellandrene + beta-myrcene + beta-pinene + diphosphate
-
-
-
?
neryl diphosphate
beta-phellandrene + diphosphate
enzyme displays a clear preference for geranyl diphosphate over neryl diphosphate
in addition, enzyme produces small quantities of limonene
-
?
additional information
?
-
no substrate: farnesyl diphosphate
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
soluble enzyme preparations from Escherichia coli BL21(DE3)/pSAG8(M), expressing (-)-beta-phellandrene synthase convert geranyl diphosphate to four products. beta-phellandrene (52%) as the major olefin, and lesser amounts of (1S,5S)-beta-pinene (34%), (1S,5S)-apinene (8.5%), and (4S)-limonene (6%) are identified. The stereochemistry of beta-phellandrene is not confirmed directly. Nevertheless, stereochemical considerations based on the established absolute configuration of the coproducts, and the natural occurrence of (4S)-beta-phellandrene in the turpentine, suggests that the biosynthetic product is the mechanistically related (4S)-antipode derived via the (3S)-linalyl diphosphate intermediate. The product of the ag8 gene is therefore designated (4S)-beta-phellandrene synthase
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
enzyme displays a clear preference for geranyl diphosphate over neryl diphosphate
in addition, enzyme produces small quantities of limonene
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
a 1,3-hydride shift from C3 to C8 of the cyclohexene nucleus is involved in the formation of phellandrene
-
-
?
geranyl diphosphate
(4S)-beta-phellandrene + diphosphate
-
some (-)-alpha-phellandrene is also formed. Both phellandrene isomers are generated from a common phellandryl cation by the cyclase
-
-
?
geranyl diphosphate
beta-phellandrene + beta-pinene + beta-myrcene + diphosphate
-
-
-
-
?
geranyl diphosphate
beta-phellandrene + beta-pinene + beta-myrcene + diphosphate
-
-
-
?
