Improved Conditions for the Production and Characterization of 1-Arylpropane-1,2-diols and Related Compounds

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概要

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• 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.

• 社団法人日本農芸化学会の論文
• 1995-12-23

著者

• Morita Hiroshi

  Department of Cardiology, Shingu Munichipal Hospital

• Hiramatsu Shigeki

  Department Of Cardiovascular Medicine Okayama University Graduated School Of Medicine Density And Ph

• Hiramatsu S

  Keio Univ. Yokohama

• 須貝 威

  慶應義塾大学理工学部

• Hiramatsu S

  Osaka Kyoiku Univ. Osaka

• Mochizuki Naoki

  Alcohol Beverage Research And Development Laboratory Asahi Breweries Ltd.

• Ohta H

  Okayama Univ. Okayama

• Ohta Hiromichi

  Department Of Chemistry Faculty Of Science And Technology Keio University

• ITOKAWA Hideji

  Department of Pharmacognosy, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences

• Itokawa H

  Department Of Pharmacognosy School Of Pharmacy Tokyo University Of Pharmacy And Life Sciences

• Itokawa Hideji

  Department Of Pharmacognosy Tokyo College Of Pharmacy

• Ohta H

  Keio Univ. Kanagawa

• Sugai Tomoharu

  Department Of Bioresource Engineering Faculty Of Agriculture Yamagata University

• SUGAI Takeshi

  Department of Chemistry, Faculty of Science and Technology, Keio University

• Ohta Hiromichi

  Department Of Applied Chemistry School Of Engineering Nagoya University

• Okazaki Hanako

  Department Of Chemistry Keio University

• Sugai Takeshi

  Department Of Agricultural Chemistry The University Of Tokyo

• Hiramatsu Shigeki

  Department Of Cardiovascular Medicine Okayama University Graduate School Of Medicine Dentistry And P

• Morita Hiroshi

  Department Of Applied Chemistry School Of Engineering Kanagawa University

• Morita Hiroshi

  Department Of Pharmacognosy Tokyo University Of Pharmacy And Life Science

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