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Polyketide: History
Please note this is an old version of this entry, which may differ significantly from the current revision.
Subjects: Chemistry, Organic
Contributor: Yu Peng

Within the context of plant-derived bioactive compounds, a polyketide is an organic natural product whose principal carbon framework is biosynthetically assembled by polyketide synthases through successive carbon–carbon bond-forming condensations of acyl-derived building blocks [1][2]. The growing carbon chain is typically generated through decarboxylative condensation reactions involving a starter acyl unit and extender units derived from malonyl or related coenzyme A substrates, producing intermediates containing characteristic carbonyl functionality [1,3]. In plants, type III polyketide synthases constitute a major enzymatic basis for this chemistry and generally operate as homodimeric enzymes that use CoA thioesters directly during iterative chain extension [3]. The resulting polyketide framework can undergo controlled cyclization, aromatization, reduction, oxidation, and other enzymatic transformations that establish its final connectivity, oxidation state, substitution pattern, and stereochemical features. The concept therefore encompasses natural-product structures defined by polyketide-chain assembly and the chemically elaborated molecular frameworks generated from that biosynthetic carbon skeleton [1][2][3].

  • Polyketide biosynthesis
  • polyketide synthase
  • acyl-CoA
  • natural products

🔵 Plant-Derived Bioactive Compounds • 🟣 Organic Chemistry • 🟡 Chemistry • 🔴 Physical Sciences

References

  1. James Staunton; Kira J. Weissman; Polyketide Biosynthesis: a Millennium Review. Nat. Prod. Rep. 2001, 18, 380-416, 10.1039/a909079g.
  2. Oliver Yu; Joseph M. Jez; Nature’s Assembly Line: Biosynthesis of Simple Phenylpropanoids and Polyketides. Plant J. 2008, 54, 750-762, 10.1111/j.1365-313x.2008.03436.x.
  3. Yan Ping Lim; Maybelle K. Go; Wen Shan Yew; Exploiting the Biosynthetic Potential of Type III Polyketide Synthases. Mol. 2016, 21, 806, 10.3390/molecules21060806.
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