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Terpene: Comparison
Please note this is a comparison between Version 2 by Yu Peng and Version 3 by Catherine Yang.

Terpenes constitute a class of natural products whose carbon skeletons are assembled from repeating five-carbon isoprene (2-methyl-1,3-butadiene) units, corresponding to the general hydrocarbon formula (C₅H₈)ₙ, in which *n* denotes the number of isoprene units incorporated [1][2]. The biosynthetic precursors of all terpene skeletons are the two isomeric five-carbon building blocks isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), which are generated through two compartmentalized routes: the cytosolic mevalonate (MVA) pathway, which begins with acetyl-CoA, and the plastid-localized 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway, which derives from pyruvate and glyceraldehyde-3-phosphate [3]. Condensation of IPP with DMAPP and subsequent chain extensions by prenyltransferases yield the prenyl diphosphate intermediates of defined chain length—geranyl diphosphate (GPP, C₁₀), farnesyl diphosphate (FPP, C₁₅), and geranylgeranyl diphosphate (GGPP, C₂₀)—that serve as the immediate substrates for terpene synthases [3]. Terpene synthases (TPS) catalyze the committed, scaffold-forming step: metal-dependent ionization of the allylic diphosphate bond generates a reactive carbocation that undergoes cyclization, hydride shifts, methyl migrations, and proton transfers to produce the hydrocarbon skeleton of the terpene. The term is defined structurally by the number of C₅ units: hemiterpenes (one unit, C₅), monoterpenes (two units, C₁₀), sesquiterpenes (three units, C₁₅), diterpenes (four units, C₂₀), sesterterpenes (five units, C₂₅), triterpenes (six units, C₃₀), and tetraterpenes (eight units, C₄₀) [1]. Within the taxonomy of biosynthesis and engineering of terpenoids, the term designates this structurally defined class of isoprenoid hydrocarbons together with the enzymatic logic of TPS-mediated skeletal diversification that generates the carbon frameworks upon which downstream oxidative and functionalizing enzymes act [4].

  • Isoprene unit
  • terpene synthase
  • MVA/MEP pathway
  • prenyl diphosphate

References

  1. Stephen G Hillier; Richard Lathe; Terpenes, hormones and life: isoprene rule revisited. J. Endocrinol. 2019, 242, R9-R22. [CrossRef]
  2. Jonathan Gershenzon; Natalia Dudareva; The function of terpene natural products in the natural world. Nat. Chem. Biol. 2007, 3, 408-414. [CrossRef]
  3. Matthew E. Bergman; Ruy W.J. Kortbeek; Michael Gutensohn; Natalia Dudareva; Plant terpenoid biosynthetic network and its multiple layers of regulation. Prog. Lipid Res. 2024, 95, 101287. [CrossRef]
  4. Joshua N. Whitehead; Nicole G. H. Leferink; Linus O. Johannissen; Sam Hay; Nigel S. Scrutton; Decoding Catalysis by Terpene Synthases. ACS Catal. 2023, 13, 12774-12802. [CrossRef]
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