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Area of Science:

  • Natural Product Chemistry
  • Biochemistry
  • Organic Chemistry

Background:

  • Piperazic acid is a non-proteinogenic amino acid found in natural products.
  • It is a cyclic hydrazine residue present in over 140 compounds across more than 30 families.
  • These compounds exhibit diverse biological activities, including anti-malarial, anti-apoptotic, and anti-bacterial properties, often with associated toxicity.

Purpose of the Study:

  • To review natural products containing piperazic acid discovered between 1959 and 2018.
  • To emphasize the biosynthetic pathways leading to these piperazic acid-containing compounds.

Main Methods:

  • Literature review of natural products containing piperazic acid.
  • Analysis of biosynthetic routes for piperazic acid formation and incorporation.
  • Identification of piperazate synthase responsible for N-N bond formation.

Main Results:

  • Over 140 piperazic acid-containing compounds from >30 families identified from 1959 to 2018.
  • Diverse biological activities reported, such as anti-malarial and anti-bacterial.
  • Recent identification of piperazate synthase, a key enzyme in piperazic acid biosynthesis.

Conclusions:

  • Piperazic acid is a significant structural motif in natural products with broad bioactivity.
  • Understanding the biosynthesis of piperazic acid is crucial for exploring these compounds.
  • Further research into piperazic acid-containing natural products may yield novel therapeutic agents.