Reductive Conversion of Carbonyl Compounds by Yeast. Part II. Improved Conditions for the Production and Characterization of 1-Arylpropane-1,2-Diols and Related Compounds

Naoki Mochizuki, Shigeki Hiramatsu, Takeshi Sugai, Hiromichi Ohta, Hiroshi Morita, Hideji Itokawa

研究成果: Article査読

23 被引用数 (Scopus)

抄録

Improved conditions for the production and characterization of 1-arylpropane-1, 2-diols and related compounds were developed. Experimental conditions providing highly enhanced activity of pyruvate decarboxylase in bakers' yeast in the presence of pyruvate, thiamine pyrophosphate, and magnesium(II)salt were applied to the preparation of (R)-1-hydroxy-1-phenyl-2-propanone from benzaldehyde. Subsequent reduction with bakers' yeast efficiently afforded 1-phenyl-1, 2-propanediol (35%). The composition of its stereoisomers was precisely determined, and the major (1R, 2S)-isomer (89% of the total mixture) could be isolated by recrystallizing the corresponding benzoate. The analytical method for identifying the stereoisomeric composition was also effective for the determination of 5-phenyl-4-pentene-2, 3-diol, the biotransformation product from cinnamaldehyde, the vinylogous substrate of benzaldehyde. Furthermore, the structural characterization of 1-(2-furyl)propane-1, 2-diol, which was obtained from furfural (28%) by the action of brewers' yeast Saccharomyces cerevisiae (carlsbergensis), is described. The major (1S, 2S)-isomer could be isolated by recrystallizing the crude product.

本文言語English
ページ(範囲)2282-2291
ページ数10
ジャーナルBioscience, Biotechnology, and Biochemistry
59
12
DOI
出版ステータスPublished - 1995

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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