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  Mechanistic studies of sesquiterpene cyclases based on their carbon isotope ratios at natural abundance

Tan, W., Bartram, S., & Boland, W. (2018). Mechanistic studies of sesquiterpene cyclases based on their carbon isotope ratios at natural abundance. Plant, Cell and Environment, 41(1), 39-49. doi:10.1111/pce.12901.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002C-1599-3 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002E-A561-B
Genre: Journal Article

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http://dx.doi.org/10.1111/pce.12901 (Publisher version)
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 Creators:
Tan, Wenhua1, 2, Author              
Bartram, Stefan1, Author              
Boland, Wilhelm1, Author              
Affiliations:
1Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society, ou_24028              
2IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society, Jena, DE, ou_421900              

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 Abstract: During the process of terpene biosynthesis, C–C bond breaking and forming steps are subjected to kinetic carbon isotope effects, leading to distinct carbon isotopic signatures of the products. Accordingly, carbon isotopic signatures could be used to reveal the ‘biosynthetic history’ of the produced terpenoids. Five known sesquiterpene cyclases, regulating three different pathways, representing simple to complex biosynthetic sequences, were heterologously expressed and used for in vitro assays with farnesyl diphosphate as substrate. Compound specific isotope ratio mass spectrometry measurements of the enzyme substrate farnesyl diphosphate (FDP) and the products of all the five cyclases were performed. The calculated δ13C value for FDP, based on δ13C values and relative amounts of the products, was identical with its measured δ13C value, confirming the reliability of the approach and the precision of measurements. The different carbon isotope ratios of the products reflect the complexity of their structure and are correlated with the frequency of carbon–carbon bond forming and breaking steps on their individual biosynthetic pathways. Thus, the analysis of carbon isotopic signatures of terpenes at natural abundance can be used as a powerful tool in elucidation of associated biosynthetic mechanisms of terpene synthases and in future in vivo studies even without ‘touching’ the plant.

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 Dates: 2017-01-032017-03-092018-01
 Publication Status: Published in print
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 Identifiers: Other: BOL667
DOI: 10.1111/pce.12901
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Title: Plant, Cell and Environment
  Other : Plant, Cell & Environment
Source Genre: Journal
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Publ. Info: Oxford, England : Blackwell Science
Pages: - Volume / Issue: 41 (1) Sequence Number: - Start / End Page: 39 - 49 Identifier: ISSN: 0140-7791
CoNE: /journals/resource/954925471334