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  Biosynthesis of an anti-addiction agent from the iboga plant

Farrow, S. C., Kamileen, M. O., Caputi, L., Bussey, K., Mundy, J. E. A., McAtee, R. C., et al. (2019). Biosynthesis of an anti-addiction agent from the iboga plant. Journal of the American Chemical Society, 141(33), 12979-12983. doi:10.1021/jacs.9b05999.

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http://dx.doi.org/10.1021/jacs.9b05999 (Publisher version)
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 Creators:
Farrow, Scott C., Author
Kamileen, Mohamed Omar1, 2, Author              
Caputi, Lorenzo1, Author              
Bussey, Kate, Author
Mundy, Julia E. A., Author
McAtee, Rory C., Author
Stephenson, Corey R. J., Author
O’Connor, Sarah E.1, Author              
Affiliations:
1Department of Natural Product Biosynthesis, Prof. Dr. Sarah O'Connor, MPI for Chemical Ecology, Max Planck Society, ou_3011808              
2IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society, Jena, DE, ou_421900              

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 Abstract: (−)-Ibogaine and (−)-voacangine are plant derived psychoactives that show promise as effective treatments for opioid addiction. However, these compounds are produced by hard to source plants making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (−)-voacangine, and de-esterified voacangine, which is converted to (−)-ibogaine by heating. This discovery will enable production of these compounds by synthetic biology methods. Notably, (−)-ibogaine and (−)-voacangine are of the opposite enantiomeric configuration compared to the other major alkaloids found in this natural product class. Discovery of these biosynthetic enzymes therefore demonstrates how nature generates both enantiomeric series of this medically important alkaloid scaffold using closely related enzymes, including those that catalyze enantioselective formal Diels-Alder reactions. One Sentence Summary Biosynthesis of iboga alkaloids with anti-addiction promise reveals enantioselectivity of enzymatic Diels-Alder reactions.

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 Dates: 2019-052019-07-312019
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: -
 Identifiers: Other: SOC088
DOI: 10.1021/jacs.9b05999
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Project name : MedPlant
Grant ID : 788301
Funding program : Horizon 2020 (H2020)
Funding organization : European Commission (EC)

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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 141 (33) Sequence Number: - Start / End Page: 12979 - 12983 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870