Biosynthesis of an Anti-Addiction Agent from the Iboga Plant

Journal of the American Chemical Society
S. FarrowSarah E. O'Connor

Abstract

(-)-Ibogaine and (-)-voacangine are plant derived psychoactives that show promise as 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, enabling biocatalytic production of these compounds. Notably, (-)-ibogaine and (-)-voacangine are of the opposite enantiomeric configuration compared to the other major alkaloids found in this natural product class. Therefore, this discovery provides insight into enantioselective enzymatic formal Diels-Alder reactions.

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Citations

Sep 21, 2019·Natural Product Reports·Robert A Hill, Andrew Sutherland
Mar 7, 2020·Natural Product Reports·Ryo TanifujiHideaki Oikawa
Aug 15, 2020·Natural Product Reports·Rishab N IyerDavid E Olson
Feb 19, 2020·Nature Chemical Biology·Lorenzo CaputiSarah E O'Connor
Aug 28, 2020·Chembiochem : a European Journal of Chemical Biology·Wadih GhattasA Jalila Simaan
Dec 17, 2019·Current Opinion in Biotechnology·Ines CarqueijeiroVincent Courdavault
Apr 29, 2021·Chemical Society Reviews·Cooper S JamiesonJohn M Billingsley
May 25, 2021·International Journal of Pharmaceutics·Adeolu Oluwasanmi, Clare Hoskins
Nov 17, 2021·Journal of the American Chemical Society·Hyeonggeun LimSunkyu Han

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