Enzymatic total synthesis of gibberellin A4 from acetate

Yoshinori Sugai, Sho Miyazaki, Shinichiro Mukai, Isamu Yumoto, Masahiro Natsume, Hiroshi Kawaide

研究成果: Article査読

10 被引用数 (Scopus)


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 isotopelabeled 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 GA 4 biosynthesis from ent-kaurene via GA12were prepared in yeast and Escherichia coli. All intermediates and the final product GA 4 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.

ジャーナルBioscience, Biotechnology and Biochemistry
出版ステータスPublished - 2011

ASJC Scopus subject areas

  • バイオテクノロジー
  • 分析化学
  • 生化学
  • 応用微生物学とバイオテクノロジー
  • 分子生物学
  • 有機化学


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