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(2E,6E)-farnesyl diphosphate + H2O = (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
(2E,6E)-farnesyl diphosphate + H2O = (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
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-
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(2E,6E)-farnesyl diphosphate + H2O = (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
reaction mechanism
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(2E,6E)-farnesyl diphosphate + H2O = (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
catalytic mechanism via intermediate is (7R)-germacra-1(10),4-diene-11-ol
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(2E,6E)-farnesyl diphosphate + H2O = (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
catalytic mechanism via intermediate is (7R)-germacra-1(10),4-diene-11-ol
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-
(2E,6E)-farnesyl diphosphate + H2O = (1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
reaction mechanism
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-
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(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germa-1(10),5-dien-11-ol + diphosphate
-
catalysed by the N-terminal domain of the bifunctional enzyme
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
2-trans,6-trans-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
additional information
?
-
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
66%
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
trans-1,10-dimethyl-trans-9-decalol
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
enzyme is essential for geosmin biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
enzyme is involved in geosmin biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
cyclization reaction, mechanism of full length enzyme and N-terminal catalytic domain
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
reaction is catalyzed by one of two sesquiterpene domains of the enzyme
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-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
enzyme is involved in geosmin biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
cyclization reaction, mechanism of full length enzyme and N-terminal catalytic domain
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
Mg-dependent conversion
-
-
?
2-trans,6-trans-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
-
key step in biosynthesis of geosmin
-
-
?
2-trans,6-trans-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
-
cyclization reaction, detailed mechanism, an intermediate is (7R)-germacra-1(10),4-diene-11-ol
GC-MS and NMR product configuration analysis
-
?
2-trans,6-trans-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
-
key step in biosynthesis of geosmin
-
-
?
2-trans,6-trans-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
-
cyclization reaction, detailed mechanism, an intermediate is (7R)-germacra-1(10),4-diene-11-ol
GC-MS and NMR product configuration analysis
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?
additional information
?
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-
no activity with geranylgeranyl diphosphate
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-
?
additional information
?
-
-
stereospecificity, the 1,3-hydride shift of the (-)-germacrene D synthase of Streptomyces coelicolor A3(2) is opposite to the enzyme from Solidago canadensis
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-
?
additional information
?
-
-
catalyzes the Mg2+-dependent cyclization of conversion of farnesyl diphosphate to a mixture of germacradienol, germacrene D, and geosmin, accompanied by small amounts of octalin
-
-
?
additional information
?
-
-
stereospecificity, the 1,3-hydride shift of the (-)-germacrene D synthase of Streptomyces coelicolor A3(2) is opposite to the enzyme from Solidago canadensis
-
-
?
additional information
?
-
-
no activity with geranylgeranyl diphosphate
-
-
?
additional information
?
-
catalyze the Mg-dependent conversion of farnesyl diphosphate to the germacradienol, an essential step in the biosynthesis of geosmin
-
-
?
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(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
2-trans,6-trans-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
additional information
?
-
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
enzyme is essential for geosmin biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
enzyme is involved in geosmin biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
-
enzyme is involved in geosmin biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(1E,4S,5E,7R)-germacra-1(10),5-dien-11-ol + diphosphate
Mg-dependent conversion
-
-
?
2-trans,6-trans-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
-
key step in biosynthesis of geosmin
-
-
?
2-trans,6-trans-farnesyl diphosphate + H2O
(4S,7R)-germacra-1(10)E,5E-dien-11-ol + diphosphate
-
key step in biosynthesis of geosmin
-
-
?
additional information
?
-
-
catalyzes the Mg2+-dependent cyclization of conversion of farnesyl diphosphate to a mixture of germacradienol, germacrene D, and geosmin, accompanied by small amounts of octalin
-
-
?
additional information
?
-
catalyze the Mg-dependent conversion of farnesyl diphosphate to the germacradienol, an essential step in the biosynthesis of geosmin
-
-
?
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He, X.; Cane, D.E.
Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2)
J. Am. Chem. Soc.
126
2678-2679
2004
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
brenda
Gust, B.; Challis, G.L.; Fowler, K.; Kieser, T.; Chater, K.F.
PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin
Proc. Natl. Acad. Sci. USA
100
1541-1546
2003
Streptomyces coelicolor
brenda
Cane, D.E.; Watt, R.M.
Expression and mechanistic analysis of a germacradienol synthase from Streptomyces coelicolor implicated in geosmin biosynthesis
Proc. Natl. Acad. Sci. USA
100
1547-1551
2003
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
brenda
Deguerry, F.; Pastore, L.; Wu, S.; Clark, A.; Chappell, J.; Schalk, M.
The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases
Arch. Biochem. Biophys.
454
123-136
2006
Pogostemon cablin (Q49SP6)
brenda
Jiang, J.; He, X.; Cane, D.E.
Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin
J. Am. Chem. Soc.
128
8128-8129
2006
Streptomyces coelicolor (Q9X839), Streptomyces coelicolor
brenda
Cane, D.E.; He, X.; Kobayashi, S.; Omura, S.; Ikeda, H.
Geosmin biosynthesis in Streptomyces avermitilis. Molecular cloning, expression, and mechanistic study of the germacradienol/geosmin synthase
J. Antibiot.
59
471-479
2006
Streptomyces avermitilis (Q82L49), Streptomyces avermitilis
brenda
Jiang, J.; Cane, D.E.
Geosmin biosynthesis. Mechanism of the fragmentation-rearrangement in the conversion of germacradienol to geosmin
J. Am. Chem. Soc.
130
428-429
2008
Streptomyces coelicolor
brenda
Ghimire, G.P.; Oh, T.J.; Lee, H.C.; Kim, B.G.; Sohng, J.K.
Cloning and functional characterization of the germacradienol synthase (spterp13) from Streptomyces peucetius ATCC 27952
J. Microbiol. Biotechnol.
18
1216-1220
2008
Streptomyces peucetius (B0FLN6)
brenda
Jiang, J.; He, X.; Cane, D.E.
Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme
Nat. Chem. Biol.
3
711-715
2007
Streptomyces coelicolor (Q9X839)
brenda