Oxidative Rearrangements of the Alkaloid Intermediate Geissoschizine.
Angewandte Chemie (International ed. in English) June 10, 2025 Mohamed O Kamileen, Benke Hong, Klaus Gase et al. 11 citations
Three cytochrome P450 enzymes in the medicinal plant Catharanthus roseus transform the central intermediate 19E-geissoschizine into four distinct alkaloid scaffolds: strychnos, sarpagan, akuammiline-type, and mavacurane-type alkaloids. In vitro enzymatic assays and gene silencing demonstrate this oxidative rearrangement. Mutational analysis shows that minimal changes to the active sites of these similar enzymes modulate product specificity. Substrate reactivity and enzyme mutations work synergistically to generate chemical diversity in monoterpene indole alkaloid biosynthesis.