Information on EC 4.2.3.118 - 2-methylisoborneol synthase

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The expected taxonomic range for this enzyme is: Bacteria

EC NUMBER
COMMENTARY hide
4.2.3.118
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RECOMMENDED NAME
GeneOntology No.
2-methylisoborneol synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(E)-2-methylgeranyl diphosphate + H2O = 2-methylisoborneol + diphosphate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2-methylisoborneol biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(E)-2-methylgeranyl-diphosphate diphosphate-lyase (cyclizing, 2-methylisoborneol-forming)
The product, 2-methylisoborneol, is a characteristc odiferous compound with a musty smell produced by soil microorganisms.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
two adjacent genes, SAM-dependent methyltransferanse gene and monoterpene cyclase gene, are responsible for geranyl diphosphate methylation and subsequent cyclization to 2-methylisoborneol in cyanobacteria
UniProt
Manually annotated by BRENDA team
Pseudanabaena limnetica Castaic Lake
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UniProt
Manually annotated by BRENDA team
two adjacent genes, SAM-dependent methyltransferanse gene and monoterpene cyclase gene, are responsible for geranyl diphosphate methylation and subsequent cyclization to 2-methylisoborneol in cyanobacteria
UniProt
Manually annotated by BRENDA team
two adjacent genes, SAM-dependent methyltransferanse gene and monoterpene cyclase gene, are responsible for geranyl diphosphate methylation and subsequent cyclization to 2-methylisoborneol in cyanobacteria
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
2-fluorolinalyl diphosphate + H2O
(1R)-(+)-camphor + HF + diphosphate
show the reaction diagram
2-methyllinalyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
geranyl diphosphate + H2O
limonene + diphosphate
show the reaction diagram
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products are 6% alpha-pinene, 23% beta-pinene , 32% limonene, 29% gamma-terpinene, and 120% delta-terpinene
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?
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.026
(E)-2-methylgeranyl diphosphate
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pH 7.0, 30C
0.0028
geranyl diphosphate
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pH 7.0, 30C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.039
(E)-2-methylgeranyl diphosphate
Streptomyces coelicolor
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pH 7.0, 30C
0.0003
geranyl diphosphate
Streptomyces coelicolor
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pH 7.0, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.45
(E)-2-methylgeranyl diphosphate
Pseudanabaena limnetica
E9NH28
temperature not specified in the publication, pH not specified in the publication
8931
PDB
SCOP
CATH
ORGANISM
UNIPROT
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
80000 - 90000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
multimer
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x * 47000, calculated
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
in complex with substrate analogues geranyl-S-thiolodiphosphate and 2-fluorogeranyl diphosphate at 1.80 and 1.95 A resolution, respectively. MIBS adopts the tertiary structure of a class I terpenoid cyclase. The dimeric quaternary structure is different, the active sites in the MIBS dimer are oriented in parallel fashion and the dimer interface in MIBS is formed by helices D1, D2
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in unliganded state and in complex with two Mg2+ ions and 2-fluoroneryl diphosphate at 1.85 and 2.00 A resolution, respectively. Cocrystallization with the fluorinated analogue of the tertiary allylic diphosphate intermediate, 2-fluorolinalyl diphosphate yields the crystal structure of the complex with the primary allylic diphosphate, 2-fluoroneryl diphosphate. The crystalline enzyme active site remains partially open, presumably due to the binding of only two Mg2+ ions
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant protein
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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expression in Streptomyces avermitilis
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
light is a crucial, but not the only, active regulatory factor for the transcription of 2-methylisoborneol synthesis genes. Under low light, there is a 30% increase in the transcription of methyltransferase and a 60% increase in methylisoborneol synthase transcription compared to controls within 312 h. Under high light intensity, however, transcription of these two genes decreases by 30% and 50%, respectively. Expression of both genes is inhibited when bacteria are cultured in the dark at 25C for 72 h
the expression level decreases at 4C, compared with at 20C
the expression level increases at 30C, compared with at 20C
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nutrition
2-methylisoborneol produced by cyanobacteria,, causes an unpleasant taste and odor in tap water. Bacterial cultures show higher accumulation of 2-methylisoborneol at 30C than at 4C or 20C after 24 h of culture