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Terpene Cyclases from Social Amoebae.

Patrick Rabe1, Jan Rinkel1, Britta Nubbemeyer1

  • 1Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.

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Summary

Social amoebae possess terpene cyclases (TCs) that synthesize unique compounds. These enzymes convert farnesyl diphosphate into specific protoilludene and asteriscadiene molecules, with mechanisms studied via labeling.

Keywords:
biosynthesisisotopesmass spectrometrysocial amoebaeterpenes

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Mycology

Background:

  • Social amoebae, like Dictyostelium discoideum, are increasingly studied for their unique biological processes.
  • Terpene cyclases (TCs) are enzymes responsible for synthesizing a vast array of natural products, but their presence and function in social amoebae were largely unexplored.

Purpose of the Study:

  • To investigate the presence and function of terpene cyclases (TCs) in social amoebae.
  • To characterize the products synthesized by TCs from Dictyostelium discoideum.
  • To elucidate the mechanisms of these TCs through enzymatic and mass spectrometry studies.

Main Methods:

  • Genome sequencing of social amoebae to identify putative terpene cyclase genes.
  • Heterologous expression and biochemical assays of identified TCs.
  • Enzymatic conversion of farnesyl diphosphate (FPP) using purified TCs.
  • Product identification and structural elucidation using Gas Chromatography-Mass Spectrometry (GC-MS) and Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Isotopic labeling experiments to study enzyme mechanisms.

Main Results:

  • Genome analysis revealed the presence of terpene cyclase genes in social amoebae.
  • Two TCs from Dictyostelium discoideum were characterized.
  • These TCs efficiently converted farnesyl diphosphate into (2S,3R,6S,9S)-(-)-protoillud-7-ene and (3S)-(+)-asterisca-2(9),6-diene.
  • Labeling experiments provided insights into the reaction mechanisms and fragmentation patterns observed in Electron Ionization Mass Spectrometry (EI-MS).

Conclusions:

  • Social amoebae harbor functional terpene cyclases with novel catalytic activities.
  • The identified TCs produce unique sesquiterpenes, expanding the known structural diversity of these natural products.
  • This study provides a foundation for understanding terpene biosynthesis in social amoebae and exploring their potential for producing valuable compounds.