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Enzymatic peptide macrocyclization via indole-N-acylation.

Hiroto Maruyama1, Yuito Yamada1, Yasuhiro Igarashi2

  • 1Faculty of Pharmaceutical Sciences, Hokkaido University Kita 12, Kita-ku Sapporo 060-0812 Japan kematsuda@pharm.hokudai.ac.jp wakimoto@pharm.hokudai.ac.jp.

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Researchers discovered BulbE TE, an enzyme that performs challenging indole N-acylation. This enzyme is crucial for synthesizing bulbiferamide and shows unique nucleophile specificity, offering insights into macrocyclization mechanisms.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Natural Product Biosynthesis

Background:

  • Indole N-acylation is a difficult chemical transformation due to the indole nitrogen's low nucleophilicity.
  • The enzymatic mechanisms underlying indole N-acylation in natural product biosynthesis are not well understood.

Purpose of the Study:

  • To elucidate the enzymatic basis of indole N-acylation in the biosynthesis of the non-ribosomal cyclopeptide bulbiferamide.
  • To characterize the enzyme BulbE TE as an N-acylindole-forming macrocyclase.

Main Methods:

  • Enzymatic assays using BulbE TE and its variants.
  • Biochemical characterization of enzyme activity and substrate scope.
  • Structural modeling of the acyl-enzyme complex.

Main Results:

  • BulbE TE catalyzes macrocyclization via indole nitrogen, primary amine, and alcohol nucleophiles.
  • The catalytic residue Cys731 is essential for indole nitrogen and alcohol nucleophilic attack.
  • A C731S variant demonstrated altered nucleophile specificity, highlighting the role of catalytic residues.

Conclusions:

  • This study provides the first enzymatic basis for indole N-acylation.
  • BulbE TE's unique catalytic mechanism and substrate specificity offer insights into TE-mediated macrocyclization.
  • The findings advance our understanding of natural product biosynthesis pathways.