| Entry |
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| Name |
pentalenene synthase;
pentalenene synthetase
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| Class |
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
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| Sysname |
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, pentalenene-forming)
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| Reaction(IUBMB) |
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate [RN: R02305]
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| Reaction(KEGG) |
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| Substrate |
(2E,6E)-farnesyl diphosphate [CPD: C00448]
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| Product |
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| Comment |
Isolated from Streptomyces avermitilis. The enzyme is involved in the biosynthesis of pentalenolactone and related antibiotics. The 9si hydrogen of farnesyl diphosphate undergoes a 1,2-hydride shift where it becomes the 1alpha hydrogen of pentalenene.
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| Pathway |
| Sesquiterpenoid and triterpenoid biosynthesis |
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| Orthology |
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| Genes |
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| Reference |
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| Authors |
Cane DE. |
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| Title |
Cell-free studies of monoterpene and sesquiterpene biosynthesis. |
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| Journal |
Biochem. Soc. Trans. 11 (1983) 510-5. |
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| Reference |
2 |
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| Authors |
Cane, D.E. and Tillman, A.M. |
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| Title |
Pentalenene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate. |
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| Journal |
J. Am. Chem. Soc. 105 (1983) 122-124. |
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| Reference |
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| Authors |
Cane DE, Sohng JK, Lamberson CR, Rudnicki SM, Wu Z, Lloyd MD, Oliver JS, Hubbard BR. |
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| Title |
Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319. |
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| Journal |
Biochemistry. 33 (1994) 5846-57. |
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| Organism |
Streptomyces sp. |
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| Reference |
|
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| Authors |
Cane DE, Abell C, Harrison PH, Hubbard BR, Kane CT, Lattman R, Oliver JS, Weiner SW |
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| Title |
Terpenoid biosynthesis and the stereochemistry of enzyme-catalysed allylic addition-elimination reactions. |
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| Journal |
Philos. Trans. R. Soc. Lond. B. Biol. Sci. 332 (1991) 123-9. |
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| Reference |
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| Authors |
Lesburg CA, Zhai G, Cane DE, Christianson DW |
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| Title |
Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. |
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| Journal |
Science. 277 (1997) 1820-4. |
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| Reference |
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| Authors |
Zu L, Xu M, Lodewyk MW, Cane DE, Peters RJ, Tantillo DJ |
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| Title |
Effect of isotopically sensitive branching on product distribution for pentalenene synthase: support for a mechanism predicted by quantum chemistry. |
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| Journal |
J. Am. Chem. Soc. 134 (2012) 11369-71. |
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| Other DBs |
ExplorEnz - The Enzyme Database: IUBMB Enzyme Nomenclature: ExPASy - ENZYME nomenclature database: BRENDA, the Enzyme Database: CAS: 90597-46-9 |
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