Development of a synthesis method for odor sesquiterpenoid, (−)-rotundone, using non-heme Fe2+-chelate catalyst and ferric-chelate reductase

Satoru Umezawa, Shunsuke Konishi, Kuniki Kino

Research output: Contribution to journalArticle

Abstract

(−)-Rotundone, a sesquiterpenoid that has a characteristic woody and peppery odor, is a key aroma component of spicy foodstuffs, such as black pepper and Australian Shiraz wine. (−)-Rotundone shows the lowest level of odor threshold in natural compounds and remarkably improves the quality of various fruit flavors. To develop a method for the synthesis of (−)-rotundone, we focused on non-heme Fe2+-chelates, which are biomimetic catalysts of the active center of oxygenases and enzymatic supply and regeneration of those catalysts. That is, we constructed a unique combination system composed of the oxidative synthesis of (−)-rotundone using the non-heme Fe2+-chelate catalyst, Fe(II)-EDTA, and the enzymatic supply and regeneration of Fe2+-chelate by ferric-chelate reductase, YqjH, from Escherichia coli. In addition, we improved the yield of (−)- rotundone by the application of cyclodextrin and glucose dehydrogenase to this system, and thus established a platform for efficient (−)-rotundone production.

Original languageEnglish
Pages (from-to)1875-1883
Number of pages9
JournalBioscience, Biotechnology and Biochemistry
Volume83
Issue number10
DOIs
Publication statusPublished - 2019 Jan 1

Fingerprint

Odors
Catalysts
Regeneration
Piper nigrum
Glucose 1-Dehydrogenase
Oxygenases
Biomimetics
Wine
Flavors
Cyclodextrins
Fruits
Escherichia coli
ferric citrate iron reductase
rotundone
Odorants
Fruit

Keywords

  • (−)-rotundone
  • Fe-chelate catalyst
  • Ferric-chelate reductase
  • Oxygenation

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Cite this

Development of a synthesis method for odor sesquiterpenoid, (−)-rotundone, using non-heme Fe2+-chelate catalyst and ferric-chelate reductase. / Umezawa, Satoru; Konishi, Shunsuke; Kino, Kuniki.

In: Bioscience, Biotechnology and Biochemistry, Vol. 83, No. 10, 01.01.2019, p. 1875-1883.

Research output: Contribution to journalArticle

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