Enzymatic Total Synthesis of Gibberellin A<sub>4</sub>from Acetate

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  • SUGAI Yoshinori
    United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology
  • MIYAZAKI Sho
    United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology
  • MUKAI Shinichiro
    Graduate School of Agriculture, Tokyo University of Agriculture and Technology
  • YUMOTO Isamu
    Graduate School of Agriculture, Tokyo University of Agriculture and Technology
  • NATSUME Masahiro
    United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology Graduate School of Agriculture, Tokyo University of Agriculture and Technology
  • KAWAIDE Hiroshi
    United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology Graduate School of Agriculture, Tokyo University of Agriculture and Technology

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  • Enzymatic Total Synthesis of Gibberellin A4 from Acetate

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Natural terpenoids have elaborate structures and various bioactivities, making difficult their synthesis and labeling with isotopes. We report here the enzymatic total synthesis of plant hormone gibberellins (GAs) with recombinant biosynthetic enzymes from stable isotope-labeled acetate. Mevalonate (MVA) is a key intermediate for the terpenoid biosynthetic pathway. 13C-MVA was synthesized from 13C-acetate via acetyl-CoA, using four enzymes or fermentation with a MVA-secreted yeast. The diterpene hydrocarbon, ent-kaurene, was synthesized from 13C-acetate and 13C-MVA with ten and six recombinant enzymes in one test tube, respectively. Four recombinant enzymes, P450 monooxygenases and soluble dioxygenases involved in the GA4 biosynthesis from ent-kaurene via GA12 were prepared in yeast and Escherichia coli. All intermediates and the final product GA4 were uniformly labeled with 13C without dilution by natural abundance when [U-13C2] acetate was used. The 13C-NMR and MS data for [U-13C20] ent-kaurene confirmed 13C-13C coupling, and no dilution with the 12C atom was observed.

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