Flavoprotein StnP2 Catalyzes the β-Carboline Formation during the Streptonigrin Biosynthesis

ACS Chem Biol. 2022 Dec 16;17(12):3499-3506. doi: 10.1021/acschembio.2c00704. Epub 2022 Nov 21.

Abstract

β-Carboline (βC) alkaloids constitute a large family of indole alkaloids that exhibit diverse pharmacological properties, such as antitumor, antiviral, antiparasitic, and antimicrobial activities. Here, we report that a flavoprotein StnP2 catalyzes the dehydrogenation at C1-N2 of a tetrahydro-β-carboline (THβC) generating a 3,4-dihydro-β-carboline (DHβC), and the DHβC subsequently undergoes a spontaneous dehydrogenation to βC formation involved in the biosynthesis of the antitumor agent streptonigrin. Biochemical characterization showed that StnP2 catalyzed the highly regio- and stereo-selective dehydrogenation, and StnP2 exhibits promiscuity toward different THβCs. This study provides an alternative kind of enzyme catalyzing the biosynthesis of βC alkaloids and enhances the importance of flavoproteins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids* / chemistry
  • Carbolines
  • Flavoproteins
  • Indole Alkaloids
  • Streptonigrin*

Substances

  • Streptonigrin
  • Flavoproteins
  • Carbolines
  • Alkaloids
  • Indole Alkaloids