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Sarpagan bridge enzyme has substrate-controlled cyclization and aromatization modes.

ABSTRACT: Cyclization reactions that create complex polycyclic scaffolds are hallmarks of alkaloid biosynthetic pathways. We present the discovery of three homologous cytochrome P450s from three monoterpene indole alkaloid-producing plants (Rauwolfia serpentina, Gelsemium sempervirens and Catharanthus roseus) that provide entry into two distinct alkaloid classes, the sarpagans and the ?-carbolines. Our results highlight how a common enzymatic mechanism, guided by related but structurally distinct substrates, leads to either cyclization or aromatization.

SUBMITTER: Dang TT

PROVIDER: S-EPMC6054303 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Sarpagan bridge enzyme has substrate-controlled cyclization and aromatization modes.

Dang Thu-Thuy T TT Franke Jakob J Carqueijeiro Ines Soares Teto IST Langley Chloe C Courdavault Vincent V O'Connor Sarah E SE

Nature chemical biology 20180625 8

Cyclization reactions that create complex polycyclic scaffolds are hallmarks of alkaloid biosynthetic pathways. We present the discovery of three homologous cytochrome P450s from three monoterpene indole alkaloid-producing plants (Rauwolfia serpentina, Gelsemium sempervirens and Catharanthus roseus) that provide entry into two distinct alkaloid classes, the sarpagans and the β-carbolines. Our results highlight how a common enzymatic mechanism, guided by related but structurally distinct substrat ...[more]

PMID: 29942076

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