A Non-Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis

Daijiro Ueda, Saori Matsugane, Wataru Okamoto, Masayuki Hashimoto, Tsutomu Sato

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Non-C5-units terpenoids (norisoprenoids) with an acetonyl group are widely distributed in nature. However, studies on the biosynthesis of norisoprenoids are scarce. Now, the C33 norisoprenoid, (all-E)-farnesylfarnesylacetone, was identified from Bacillus spp. and it was elucidated for the first time that superoxide mediates the cleavage of menaquinones (vitamin K) to form norisoprenoids in saponification treatment. From in vivo experiments using gene-disrupted Bacillus subtilis strains targeted for enzymes responsible for menaquinone biosynthesis and for superoxide dismutase, it was suggested that the non-enzymatic cleavage (autoxidation) of menaquinone with superoxide resulted in norisoprenoid synthesis in Bacillus cells. Furthermore, the bioactive norisoprenoids, farnesylacetone and phytone, were produced in Bacillus cells by this novel synthesis system.

Original languageEnglish
Pages (from-to)10347-10351
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number32
DOIs
Publication statusPublished - 2018 Aug 6

Fingerprint

Norisoprenoids
Terpenes
Bacilli
Superoxides
Vitamin K 2
Biosynthesis
Saponification
Vitamins
Enzymes
Vitamin K
Genes
Superoxide Dismutase
Experiments

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Ueda, Daijiro ; Matsugane, Saori ; Okamoto, Wataru ; Hashimoto, Masayuki ; Sato, Tsutomu. / A Non-Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 32. pp. 10347-10351.
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A Non-Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis. / Ueda, Daijiro; Matsugane, Saori; Okamoto, Wataru; Hashimoto, Masayuki; Sato, Tsutomu.

In: Angewandte Chemie - International Edition, Vol. 57, No. 32, 06.08.2018, p. 10347-10351.

Research output: Contribution to journalArticle

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