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IUBMB Comments The enzyme, found in the bacterium Streptomyces viridochromogenes, is specific for (2E,6E)-farnesyl diphosphate and produces only (-)-alpha-amorphene.
The enzyme appears in viruses and cellular organisms
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(2E,6E)-farnesyl diphosphate = (-)-alpha-amorphene + diphosphate
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(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, (-)-alpha-amorphene-forming)
The enzyme, found in the bacterium Streptomyces viridochromogenes, is specific for (2E,6E)-farnesyl diphosphate and produces only (-)-alpha-amorphene.
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(2E,6E)-farnesyl diphosphate
(-)-alpha-amorphene + diphosphate
(2E,6E)-farnesyl diphosphate
(-)-alpha-amorphene + diphosphate
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(-)-alpha-amorphene i.e. (1S,4aR,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene. Initial 1,6-cyclisation
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(2E,6E)-farnesyl diphosphate
(-)-alpha-amorphene + diphosphate
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(-)-alpha-amorphene i.e. (1S,4aR,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene. Initial 1,6-cyclisation. Incubations with geranyl diphosphate and geranylgeranyl diphosphate gives no products
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(2E,6E)-farnesyl diphosphate
(-)-alpha-amorphene + diphosphate
-
(-)-alpha-amorphene i.e. (1S,4aR,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene. Initial 1,6-cyclisation. Incubations with geranyl diphosphate and geranylgeranyl diphosphate gives no products
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?
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(2E,6E)-farnesyl diphosphate
(-)-alpha-amorphene + diphosphate
-
(-)-alpha-amorphene i.e. (1S,4aR,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene. Initial 1,6-cyclisation
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?
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UniProt
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UniParc: UPI0001B4D949
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UniProt
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UniParc: UPI0001B4D949
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AAMS_STRVT
Streptomyces viridochromogenes (strain DSM 40736 / JCM 4977 / BCRC 1201 / Tue 494)
338
0
37003
Swiss-Prot
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A0A6I1Z753_9ACTN
338
0
37269
TrEMBL
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expression in Escherichia coli
expression in Escherichia coli BL21
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Rabe, P.; Dickschat, J.S.
Rapid chemical characterization of bacterial terpene synthases
Angew. Chem. Int. Ed. Engl.
52
1810-1812
2013
Streptomyces viridochromogenes (D9XDR8), Streptomyces viridochromogenes DSM 40736 (D9XDR8)
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Rinkel, J.; Rabe, P.; Garbeva, P.; Dickschat, J.S.
Lessons from 1,3-hydride shifts in sesquiterpene cyclizations
Angew. Chem. Int. Ed. Engl.
55
13593-13596
2016
Streptomyces viridochromogenes, Streptomyces viridochromogenes DSM 40736
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Rabe, P.; Schmitz, T.; Dickschat, J.S.
Mechanistic investigations on six bacterial terpene cyclases
Beilstein J. Org. Chem.
12
1839-1850
2016
Streptomyces viridochromogenes
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History
Enzyme Nomenclature
4.2.3.162 (-)-alpha-amorphene synthase
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