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(E)-2-methylgeranyl diphosphate + H2O
2-methylisoborneol + diphosphate
2-fluorolinalyl diphosphate + H2O
(1R)-(+)-camphor + HF + diphosphate
2-methyllinalyl diphosphate + H2O
2-methylisoborneol + diphosphate
2-methylneryl diphosphate + H2O
2-methyllimonene
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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additional information
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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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(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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(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
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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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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-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-methyllinalyl diphosphate + H2O
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
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2-methylneryl diphosphate + H2O
2-methyllimonene
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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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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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physiological function
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
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
2-methylisoborneol (2-MIB) has a muddy smell with a low odor and flavor threshold and is a contaminant of drinking water, wine and fish. Moreover it is related to the musty-earthy aroma in camembert and brie
physiological function
2-methylisoborneol (2-MIB) has a muddy smell with a low odor and flavor threshold and is a contaminant of drinking water, wine and fish. Moreover it is related to the musty-earthy aroma in camembert and brie
physiological function
geosmin and 2-methylisoborneol (MIB) are muddy/earthy off-flavor metabolites produced by a range of bacteria. Cyanobacteria are the major producers of the volatile metabolites geosmin and MIB which produce taste and odor problems in drinking water and fish worldwide
physiological function
geosmin and 2-methylisoborneol (MIB) are muddy/earthy off-flavor metabolites produced by a range of bacteria. Cyanobacteria are the major producers of the volatile metabolites geosmin and MIB which produce taste and odor problems in drinking water and fish worldwide
physiological function
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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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physiological function
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2-methylisoborneol (2-MIB) has a muddy smell with a low odor and flavor threshold and is a contaminant of drinking water, wine and fish. Moreover it is related to the musty-earthy aroma in camembert and brie
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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 4°C, compared with at 20°C
the expression level increases at 30°C, compared with at 20°C
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
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
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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Giglio, S.; Chou, W.K.; Ikeda, H.; Cane, D.E.; Monis, P.T.
Biosynthesis of 2-methylisoborneol in cyanobacteria
Environ. Sci. Technol.
45
992-998
2010
Pseudanabaena limnetica (E9NH28), Pseudanabaena limnetica, Pseudanabaena limnetica Castaic Lake (E9NH28)
brenda
Wang, C.M.; Cane, D.E.
Biochemistry and molecular genetics of the biosynthesis of the earthy odorant methylisoborneol in Streptomyces coelicolor
J. Am. Chem. Soc.
130
8908-8909
2008
Streptomyces coelicolor (Q9F1Y6), Streptomyces coelicolor
brenda
Wang, Z.; Xu, Y.; Shao, J.; Wang, J.; Li, R.
Genes associated with 2-methylisoborneol biosynthesis in cyanobacteria: isolation, characterization, and expression in response to light
PLoS One
6
e18665
2011
Pseudanabaena sp. (G0YUP1), Pseudanabaena sp., Planktothricoides raciborskii (G0YUP5), Pseudanabaena sp. dqh15 (G0YUP1)
brenda
Komatsu, M.; Tsuda, M.; Omura, S.; Oikawa. H.; Ikeda, H.
Identification and functional analysis of genes controlling biosynthesis of 2-methylisoborneol
Proc. Natl. Acad. Sci. USA
105
7422-7427
2008
Streptomyces lasalocidi (D3KYU2), Streptomyces lasalocidi
brenda
Koeksal, M.; Chou, W.K.; Cane, D.E.; Christianson, D.W.
Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate
Biochemistry
51
3011-3020
2012
Streptomyces coelicolor (Q9F1Y6), Streptomyces coelicolor
brenda
Koeksal, M.; Chou, W.K.; Cane, D.E.; Christianson, D.W.
Unexpected reactivity of 2-fluorolinalyl diphosphate in the active site of crystalline 2-methylisoborneol synthase
Biochemistry
52
5247-5255
2013
Streptomyces coelicolor (Q9F1Y6), Streptomyces coelicolor A3(2) (Q9F1Y6), Streptomyces coelicolor A3(2)
brenda
Kakimoto, M.; Ishikawa, T.; Miyagi, A.; Saito, K.; Miyazaki, M.; Asaeda, T.; Yamaguchi, M.; Uchimiya, H.; Kawai-Yamada, M.
Culture temperature affects gene expression and metabolic pathways in the 2-methylisoborneol-producing cyanobacterium Pseudanabaena galeata
J. Plant Physiol.
171
292-300
2014
Pseudanabaena galeata (U6C722), Pseudanabaena galeata
brenda
Chou, W.K.; Gould, C.A.; Cane, D.E.
Incubation of 2-methylisoborneol synthase with the intermediate analog 2-methylneryl diphosphate
J. Antibiot.
70
625-631
2017
Streptomyces coelicolor (Q9F1Y6), Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145 (Q9F1Y6)
brenda
Kschowak, M.J.; Wortmann, H.; Dickschat, J.S.; Schrader, J.; Buchhaupt, M.
Heterologous expression of 2-methylisoborneol / 2 methylenebornane biosynthesis genes in Escherichia coli yields novel C11-terpenes
PLoS ONE
13
e0196082
2018
Streptomyces griseus subsp. griseus (Q9F1V8), Streptomyces coelicolor (Q9F1Y6), Streptomyces coelicolor ATCC BAA-471 / A3(2) / M145 (Q9F1Y6)
brenda
Suurnaekki, S.; Gomez-Saez, G.; Rantala-Ylinen, A.; Jokela, J.; Fewer, D.; Sivonen, K.
Identification of geosmin and 2-methylisoborneol in cyanobacteria and molecular detection methods for the producers of these compounds
Water Res.
68
56-66
2015
Planktothrix sp. 328 (A0A0A7HKJ5), Oscillatoria sp. 327/2 (A0A0A7HMM5)
brenda