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Structural Basis for Cyclic Terpene Biosynthesis by Tobacco 5-Epi-Aristolochene Synthase
Abstract
Terpene cyclases catalyze the synthesis of cyclic terpenes with 10-, 15-, and 20-carbon acyclic isoprenoid diphosphates as substrates. Plants have been a source of these natural products by providing a homologous set of terpene synthases. The crystal structures of 5-epi-aristolochene synthase, a sesquiterpene cyclase from tobacco, alone and complexed separately with two farnesyl diphosphate analogs were analyzed. These structures reveal an unexpected enzymatic mechanism for the synthesis of the bicyclic product, 5-epi-aristolochene, and provide a basis for understanding the stereochemical selectivity displayed by other cyclases in the biosynthesis of pharmacologically important cyclic terpenes. As such, these structures provide templates for the engineering of novel terpene cyclases.
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Citations
Cited by
Structural Biology and Chemistry of the Terpenoid Cyclases
Christianson, D. W. (2006) · Chemical Reviews · doi:10.1021/cr050286w · Cited by 788
Biogenesis, molecular regulation and function of plant isoprenoids.
Bouvier, F., Rahier, A., & Camara, B. (2005) · Progress in Lipid Research · doi:10.1016/j.plipres.2005.09.003 · Cited by 498
Köllner, T. G., Held, M., Lenk, C., Hiltpold, I., Turlings, T. C. J., Gershenzon, J., & Degenhardt, J. (2008) · The Plant Cell · doi:10.1105/tpc.107.051672 · Cited by 470
Mercke, P., Bengtsson, M., Bouwmeester, H. J., Posthumus, M. A., & Brodelius, P. E. (2000) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.2000.1962 · Cited by 283
Chang, Y.-J., Song, S.-H., Park, S.-H., & Kim, S.-U. (2000) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.2000.2061 · Cited by 154
Metadata
- Authors
- Starks, C. M., Back, K., Chappell, J., & Noel, J. P.
- Venue
- Science
- Published
- 1997-09-19
- Volume
- 277
- Issue
- 5333
- Pages
- 1815-1820
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2080690387
- Cited by
- 749
- References
- 0
- FWCI
- 8.44
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Structural Basis for Cyclic Terpene Biosynthesis by Tobacco 5-Epi-Aristolochene Synthase. https://app.cochat.ai/papers/10.1126/science.277.5333.1815
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- Starks, C. M., Back, K., Chappell, J., & Noel, J. P. (1997). Structural Basis for Cyclic Terpene Biosynthesis by Tobacco 5-Epi-Aristolochene Synthase. Science. https://doi.org/10.1126/science.277.5333.1815
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