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Stereoselective oxidation of racemic 1-arylethanols by basil cultured cells of Ocimum basilicum cv. Purpurascens
Authors:Ken-ichi Itoh  Kaoru Nakamura  Takamitsu Utsukihara  Hiroshi Sakamaki  C. Akira Horiuchi
Affiliation:(1) College of Science and Technology, Nihon University, 7-24-1 Narashinodai, Funabashi-shi Chiba, 274-8501, Japan;(2) Institute for Chemical Research, Kyoto University, Uji-shi Kyoto, 611-0011, Japan;(3) Department of Chemistry, Rikkyo (St. Paul’s) University, Nishi-ikebukuro, Toshima-ku Tokyo, 171-8501, Japan
Abstract:The biotransformation of racemic 1-phenylethanol (30 mg) with plant cultured cells of basil (Ocimum basilicum cv. Purpurascens, 5 g wet wt) by shaking 120 rpm at 25°C for 7 days in the dark gave (R)-(+)-1-phenylethanol and acetophenone in 34 and 24% yields, respectively. The biotransformation can be applied to other 1-arylethanols and basil cells oxidized the (S)-alcohols to the corresponding ketones remaining the (R)-alcohols in excellent ee.
Keywords:1-Arylethanols  Basil ketones   Ocimum basilicum cv. Purpurascens   (R)-Alcohols  Stereoselective oxidation
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