Information on EC 4.2.3.117 - (-)-camphene synthase

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The expected taxonomic range for this enzyme is: Spermatophyta

EC NUMBER
COMMENTARY
4.2.3.117
-
RECOMMENDED NAME
GeneOntology No.
(-)-camphene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = (-)-camphene + diphosphate
show the reaction diagram
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
oleoresin monoterpene volatiles biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-camphene-forming]
(-)-Camphene is the major product in Abies grandis (grand fir) with traces of other monoterpenoids [1]. In Pseudotsuga menziesii (Douglas-fir) there are about equal parts of (-)-camphene and (-)-alpha-pinene with traces of four other monoterpenoids [2,3]. In Solanum lycopersicum (tomato) tricyclene, beta-myrcene, limonene, and traces of several other monoterpenoids are also formed [4]. See also EC 4.2.3.15 myrcene synthase, EC 4.2.3.16 (4S)-limonene synthase, EC 4.2.3.119 (-)-alpha-pinene synthase and EC 4.2.3.105 tricyclene synthase.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3R)-linalyl diphosphate
(+)-camphene + diphosphate
show the reaction diagram
-
(3S)-enantiomer is preferred over (3R)-enantiomer
products are (-)-camphene and (-)alpha-pinene
-
?
(3S)-linalyl diphosphate
(+)-camphene + diphosphate
show the reaction diagram
-
(3S)-enantiomer is preferred over (3R)-enantiomer
products are (+)-camphene and (+)-alpha-pinene
-
?
geranyl diphosphate
(-)-camphene + diphosphate
show the reaction diagram
-
-
25% (-)-alpha-pinene, 31% (-)-camphene, 24% (-)beta-pinene
-
?
geranyl diphosphate
(-)-camphene + diphosphate
show the reaction diagram
Q4QSN3
-
main products (-)-camphene and (-)-alpha-pinene, minor products 3-carene, beta-pinene and limonene
-
?
geranyl diphosphate
(-)-camphene + diphosphate
show the reaction diagram
-
-
products are (-)-alpha-pinene, (-)-beta-pinene, and (-)-camphene
-
?
geranyl diphosphate
(-)-camphene + diphosphate
show the reaction diagram
-
-
products are (-)-camphene and (-)alpha-pinene
-
?
geranyl diphosphate
(-)-camphene + diphosphate
show the reaction diagram
-
-
products are (-)-camphene, (-)-alpha-pinene, (-)-beta-pinene, (-)-limonene and myrcene
-
?
neryl diphosphate
(-)-camphene + diphosphate
show the reaction diagram
-
-
products are (-)-camphene and (-)-alpha-pinene
-
?
geranyl diphosphate
(-)-camphene + diphosphate
show the reaction diagram
-
-
products are 54% (-)-(1S,4R)-camphene, followed by 32% (-)-(1S,5S)-alpha-pinene and 7% (-)-(4S)-limonene
-
?
additional information
?
-
-
each product exhibits the same absolute configuration at the center derived from C-6 of geranyl diphosphate, i e. the isopropylidene-substituted carbon
-
-
-
additional information
?
-
-
enzymes removes the C4-proS-hydrogen of the substrate, the C3 proton of the corresponding pinyl cation, with a stereoselectivity exceeding 78% 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
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
-
or Mn2+, required. Mg2+ is preferred over Mn2+
Mn2+
-
or Mn2+, required. Mg2+ is preferred over Mn2+, Mn2+ shows 60-70% of the activity with Mg2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-hydroxymercuribenzoate
-
-
diphosphate
-
-
N-ethylmaleimide
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.5
-
or below, isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
immature leaf
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
95000
-
gel filtration
717749
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 70750, calculated
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
proteolytic modification
-
sequence contains a putative N-terminal targeting peptide
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
modeling of amino acid sequence onto the crystal structures of tobacco 5-epi-aristolochene synthase and bornyl diphosphate synthase and comparison with (-)-pinene synthase
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
-
expression in Escherichia coli
Q4QSN3
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
replacement of selected amino acid residues in (-)-pinene synthase with the corresponding residues from (-)-camphene synthase in an effort to identify the amino acids responsible for the catalytic differences. The approach produces an enzyme in which more than half of the product is channeled through an alternative pathway. Several (-)-pinene synthase to (-)-camphene synthase amino acid substitutions are necessary before catalysis is significantly altered