ArticleChembiochem : a European journal of chemical biology2026
Chemoenzymatic Synthesis of (4R,7R)-Zingiberene Enables Construction of nor-Sesquiterpene Semiochemical Analogs.
Article in Chembiochem : a European journal of chemical biology, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The wild tomato sesquiterpene (4R,7R)-zingiberene (6a) acts as a potent repellent of the economically important agricultural pest, the silverleaf whitefly (Bemisia tabaci). While its biosynthesis is catalyzed by 7-epi-zingiberene synthase from the noncanonical terpene precursor (2Z,6Z)-farnesyl pyrophosphate (5a), the precise enzymatic mechanism has remained undetermined. Using deuterated substrates generated chemoenzymatically, the 1,6-cyclization mechanism was established to proceed via a 1,3-hydride shift from the C1 position of the initial bisabolyl carbocationic intermediate. Product diversity was expanded by identifying two single residue switches within the G1/2 helix that govern enzyme fidelity, thereby redirecting product distributions to alternative C6-cyclized zingiberenols as well as γ- and β-curcumene. Applying this chemoenzymatic synthesis with alternative allyl alcohols plus isoprenol enabled the production and structural diversification of two novel nor-sesquiterpene analogs (C
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