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
4.2.3.118
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RECOMMENDED NAME
GeneOntology No.
2-methylisoborneol synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(E)-2-methylgeranyl diphosphate + H2O = 2-methylisoborneol + diphosphate
show the reaction diagram
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-
-
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PATHWAY
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.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
2-MIB cyclase
-
-
-
-
2-MIB synthase
D3KYU2
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MIB synthase
-
-
-
-
MIBS
-
-
-
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MIBS
Pseudanabaena limnetica Castaic Lake
E9NH28
-
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monoterpene cyclase
G0YUP5
-
monoterpene cyclase
G0YUP1
-
monoterpene cyclase
G0YUP1
-
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sco7700
-
-
-
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ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
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
-
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 ACCESSION NO.
COMMENTARY
LITERATURE
physiological function
E9NH28
biosynthesis of 2-methylisoborneol in cyanobacteria is a result of 2 key reactions, a S-adenosylmethionine-dependent methylation of the monoterpene precursor geranyl diphosphate to 2-methylgeranyl diphosphate catalyzed by geranyl diphosphate 2-methyltransferase, and further cyclization of 2-methylgeranyl diphosphate to 2-methylisoborneol catalyzed by 2-methylisoborneol synthase as part of a 2-methylisoborneol operon
physiological function
D3KYU2, -
biosynthetic pathway to 2-methylisoborneol involves the methylation of geranyl diphosphate by GPP methyltransferase and its subsequent cyclization by monoterpene cyclase to 2-methylisoborneol
physiological function
Pseudanabaena limnetica Castaic Lake
-
biosynthesis of 2-methylisoborneol in cyanobacteria is a result of 2 key reactions, a S-adenosylmethionine-dependent methylation of the monoterpene precursor geranyl diphosphate to 2-methylgeranyl diphosphate catalyzed by geranyl diphosphate 2-methyltransferase, and further cyclization of 2-methylgeranyl diphosphate to 2-methylisoborneol catalyzed by 2-methylisoborneol synthase as part of a 2-methylisoborneol operon
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SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
D3KYU2, -
-
-
-
?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
G0YUP1, -
-
-
-
?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
G0YUP5
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-
-
?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
E9NH28
-
major reaction product
-
?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
Q9F1Y6
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plus trace amounts of 2-methylbornene
-
?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
G0YUP1
-
-
-
?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
show the reaction diagram
Pseudanabaena limnetica Castaic Lake
E9NH28
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major reaction product
-
?
geranyl diphosphate + H2O
limonene + diphosphate
show the reaction diagram
Q9F1Y6
-
products are 6% alpha-pinene, 23% beta-pinene , 32% limonene, 29% gamma-terpinene, and 120% delta-terpinene
-
?
additional information
?
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Q9F1Y6
cyclization of (E)-2-methylgeranyl diphosphate most likely occurs by a mechanism closely resembling that established for the conversion of geranyl diphosphate to bornyl diphosphate, except that the penultimate bornyl cation is quenched on the exo face by water, analogous to the formation of fenchol, rather than by internal return of the diphosphate to the endo face, no substrate: farnesyl diphosphate, geranylgeranyl diphosphate
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METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
D3KYU2, -
required
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.026
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(E)-2-methylgeranyl diphosphate
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pH 7.0, 30C
0.0028
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geranyl diphosphate
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pH 7.0, 30C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.039
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(E)-2-methylgeranyl diphosphate
-
pH 7.0, 30C
0.0003
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geranyl diphosphate
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pH 7.0, 30C
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
1.45
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(E)-2-methylgeranyl diphosphate
E9NH28
temperature not specified in the publication, pH not specified in the publication
316221
PDB
SCOP
CATH
ORGANISM
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
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
80000
90000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-
x * 49937, MALDI-TOF
?
D3KYU2, -
x * 52400, SDS-PAGE, His-tagged recombinant protein
multimer
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x * 47000, calculated
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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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Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
recombinant protein
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Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli
Q9F1Y6
expression in Streptomyces avermitilis
D3KYU2, -
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
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
G0YUP5
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
G0YUP1, -
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
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