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

Research output: Contribution to journalArticle

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Abstract

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,25)-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.

Original languageEnglish
Pages (from-to)2282-2291
Number of pages10
JournalBioscience, Biotechnology and Biochemistry
Volume59
Issue number2
Publication statusPublished - 1995

Fingerprint

Yeast
Saccharomyces cerevisiae
Isomers
Pyruvate Decarboxylase
Furaldehyde
Thiamine Pyrophosphate
Propane
Propylene Glycol
Stereoisomerism
Benzoates
Alkenes
Biotransformation
Chemical analysis
Pyruvic Acid
Magnesium
Salts
Substrates
benzaldehyde

ASJC Scopus subject areas

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

Cite this

Improved conditions for the production and characterization of 1-arylpropane-1,2-diols and related compounds. / Mochizuki, Naoki; Hiramatsu, Shigeki; Sugai, Takeshi; Ohta, Hiromichi; Morita, Hiroshi; Itokawa, Hideji.

In: Bioscience, Biotechnology and Biochemistry, Vol. 59, No. 2, 1995, p. 2282-2291.

Research output: Contribution to journalArticle

Mochizuki, Naoki ; Hiramatsu, Shigeki ; Sugai, Takeshi ; Ohta, Hiromichi ; Morita, Hiroshi ; Itokawa, Hideji. / Improved conditions for the production and characterization of 1-arylpropane-1,2-diols and related compounds. In: Bioscience, Biotechnology and Biochemistry. 1995 ; Vol. 59, No. 2. pp. 2282-2291.
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