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Ribosomal peptides with polycyclic isoprenoid moieties.

Florian Hubrich1,2, Sanath K Kandy3, Clara Chepkirui1

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Scientists discovered new ways to modify peptides using complex, cyclized terpene units, which are crucial for their anti-cyanobacterial activity and have broad biotechnological potential.

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Area of Science:

  • Biochemistry
  • Natural Products Chemistry
  • Molecular Biology

Background:

  • Isoprenoid modifications (prenylation) are vital for protein and peptide functions, with farnesyl and geranylgeranyl being common.
  • Ribosomal peptide prenylation typically involves smaller isoprenoid units than those found in proteins.
  • Cyclized terpene modifications in biomolecules have not been previously reported.

Purpose of the Study:

  • To identify novel ribosomally synthesized and post-translationally modified peptides (RiPPs) with unique isoprenoid modifications.
  • To investigate the enzymes responsible for installing these elaborate modifications.
  • To explore the biological activity and biotechnological applications of these modified peptides.

Main Methods:

  • Targeted genome mining to identify relevant gene clusters.
  • Heterologous pathway reconstitution in a suitable host organism.
  • Biochemical characterization of bifunctional maturases (prenyltransferase-terpene cyclase fusions).
  • Structural elucidation of the modified peptide product.
  • Bioassays to assess biological activity.

Main Results:

  • Discovery of RiPPs with complex, cyclized geranylgeranyl modifications, a previously unreported modification type.
  • Identification of novel bifunctional maturases with fused prenyltransferase and terpene cyclase domains.
  • Characterization of a cyanobacterial proteusin with a pseudosteroid-annelated polycyclic peptide structure.
  • Demonstration that the isoprenoid modification is essential for the observed modest anti-cyanobacterial activity.

Conclusions:

  • This study reveals a new class of cyclized isoprenoid-modified peptides (RiPPs).
  • The identified maturases possess unique fused prenyltransferase-terpene cyclase architectures.
  • The findings expand the known repertoire of natural product modifications and suggest broad applicability in biotechnology.
  • Cyclic isoprenoid units are predicted in diverse RiPP families, highlighting the system's versatility.