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  Dual catalytic activity of a cytochrome P450 controls bifurcation at a metabolic branch point of alkaloid biosynthesis in Rauwolfia serpentina

Dang, T.-T.-T., Franke, J., Tatsis, E., & O'Connor, S. E. (2017). Dual catalytic activity of a cytochrome P450 controls bifurcation at a metabolic branch point of alkaloid biosynthesis in Rauwolfia serpentina. Angewandte Chemie International Edition, 56(32), 9440-9444. doi:10.1002/anie.201705010.

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http://dx.doi.org/10.1002/anie.201705010 (Publisher version)
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 Creators:
Dang, Thu-Thuy T.1, Author
Franke, Jakob1, Author
Tatsis, Evangelos1, Author
O'Connor, Sarah E.1, Author           
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1external, ou_persistent22              

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Free keywords: MONOTERPENOID INDOLE ALKALOIDS; PLANT-CELL CULTURES; RAUVOLFIA-SERPENTINA; AJMALINE PATHWAY; 1ST EXAMPLE; EXPRESSION; FAMILY; ENZYME; PURIFICATION; GLUCOSIDASEChemistry; alkaloids; biosynthesis; cytochrome p450s; perakine; vomilenine;
 Abstract: Plants create tremendous chemical diversity from a single biosynthetic intermediate. In plant-derived ajmalan alkaloid pathways, the biosynthetic intermediate vomilenine can be transformed into the anti-arrhythmic compound ajmaline, or alternatively, can isomerize to form perakine, an alkaloid with a structurally distinct scaffold. Here we report the discovery and characterization of vinorine hydroxylase, a cytochrome P450 enzyme that hydroxylates vinorine to form vomilenine, which was found to exist as a mixture of rapidly interconverting epimers. Surprisingly, this cytochrome P450 also catalyzes the non-oxidative isomerization of the ajmaline precursor vomilenine to perakine. This unusual dual catalytic activity of vinorine hydroxylase thereby provides a control mechanism for the bifurcation of these alkaloid pathway branches. This discovery highlights the unusual catalytic functionality that has evolved in plant pathways.

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Language(s): eng - English
 Dates: 2017
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: Other: SOC067
DOI: 10.1002/anie.201705010
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Title: Angewandte Chemie International Edition
  Other : Angewandte Chemie, International Edition
  Other : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 56 (32) Sequence Number: - Start / End Page: 9440 - 9444 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851