期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 32, 页码 9440-9444出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201705010
关键词
alkaloids; biosynthesis; cytochrome p450s; perakine; vomilenine
资金
- EMBO Long Term Fellowship [ALTF 739-2015]
- DFG [FR 3720/1-1]
- BBSRC [BBS/E/J/000CA512, BB/N007905/1, BBS/E/J/000PR9790] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BB/N007905/1, BBS/E/J/000CA512, BBS/E/J/000PR9790] Funding Source: researchfish
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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