4.2.3.118: 2-methylisoborneol synthase
This is an abbreviated version!
For detailed information about 2-methylisoborneol synthase, go to the full flat file.
Reaction
Synonyms
2-MIB cyclase, 2-MIB synthase, MIB synthase, MIBS, MIBSg, monoterpene cyclase, sco7700
ECTree
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Substrates Products
Substrates Products on EC 4.2.3.118 - 2-methylisoborneol synthase
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REACTION DIAGRAM
geranyl diphosphate + H2O
limonene + diphosphate
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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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?
2-methylisoborneol + diphosphate
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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major reaction product
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(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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major reaction product
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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-
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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plus trace amounts of 2-methylbornene
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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-
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?
(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
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?
(1R)-(+)-camphor + HF + diphosphate
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single cyclic product, obtained via the (4R)-alpha-2-fluoroterpinyl carbocation intermediate. The initially generated 2-fluoroisoborneol cyclization product is unstable and undergoes elimination of hydrogen fluoride to yield (1R)-(+)-camphor
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?
2-fluorolinalyl diphosphate + H2O
(1R)-(+)-camphor + HF + diphosphate
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single cyclic product, obtained via the (4R)-alpha-2-fluoroterpinyl carbocation intermediate. The initially generated 2-fluoroisoborneol cyclization product is unstable and undergoes elimination of hydrogen fluoride to yield (1R)-(+)-camphor
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?
2-methylisoborneol + diphosphate
natural intermediate of the cyclization reaction
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2-methyllinalyl diphosphate + H2O
2-methylisoborneol + diphosphate
natural intermediate of the cyclization reaction
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?
2-methylneryl diphosphate + H2O
2-methyllimonene
Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145
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GC-MS analysis for product identification and quantification
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additional information
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GC-MS analysis for product identification and quantification
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additional information
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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
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?
additional information
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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
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additional information
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no substrate: farnesyl diphosphate, geranylgeranyl diphosphate
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additional information
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no substrate: farnesyl diphosphate, geranylgeranyl diphosphate
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