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Controlling a structural branch point in ergot alkaloid biosynthesis.

Johnathan Z Cheng1, Christine M Coyle, Daniel G Panaccione

  • 1Massachusetts Institute of Technology, Department of Chemistry, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.

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Area of Science:

  • Biochemistry
  • Mycology
  • Natural Product Synthesis

Background:

  • Ergot alkaloids are fungal-derived indole alkaloids with significant pharmacological effects.
  • Chanoclavine-I aldehyde is a key branch point intermediate in ergot alkaloid biosynthesis.
  • Futuclavine and agroclavine are ergot alkaloids derived from alternate pathways originating from chanoclavine-I aldehyde.

Purpose of the Study:

  • To investigate the enzymatic activity of Old Yellow Enzyme homologues in ergot alkaloid biosynthesis.
  • To elucidate the mechanism controlling the branch point in ergot alkaloid production.
  • To understand the divergence in pathways leading to festuclavine and agroclavine.

Main Methods:

  • Enzymatic assays using purified EasA homologues.
  • Analysis of products derived from chanoclavine-I aldehyde.
  • Mutational analysis of EasA enzymes.

Main Results:

  • Aspergillus fumigatus EasA catalyzes the conversion of chanoclavine-I aldehyde to festuclavine.
  • Neotyphodium lolii EasA produces agroclavine from chanoclavine-I aldehyde.
  • Mutational studies provided insights into the mechanistic basis for the observed switch in enzymatic activity.

Conclusions:

  • The Old Yellow Enzyme homologue EasA plays a critical role in directing ergot alkaloid biosynthesis.
  • Variations in EasA enzyme structure and function dictate the specific ergot alkaloid produced at a key biosynthetic branch point.
  • Understanding these mechanisms can inform the targeted production of specific ergot alkaloids.