Highly stereoselective preparation of (3R,4S)-3,4-chromanediol by deracemization of (±)-3-hydroxy-4-chromanone by Trichosporon cutaneum |
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| Affiliation: | 1. Department of Organic Chemistry, Campinas State University, CP 6154, 13084-971 Campinas-SP, Brazil;2. Department of Basic Sciences, Faculty of Animal Science and Food Engineering, University of São Paulo, CP23, 13635-900, Pirassununga-SP, Brazil;1. Department of Physics, College of Science, King Khalid University, P.O. Box 9004, Abha, 61413, Saudi Arabia;2. TEMA-NRD, Department of Mechanical Engineering and Aveiro Institute of Nanotechnology (AIN), University of Aveiro, 3810-193, Aveiro, Portugal;3. Department of Materials Engineering and Ceramic, CICECO, University of Aveiro, 3810-193, Aveiro, Portugal;4. National Research University of Electronic Technology “MIET”, 124498 Moscow, Russia;1. Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, PO Box 537, SI-1000 Ljubljana, Slovenia;2. EN-FIST Centre of Excellence, Dunajska 156, SI-1000 Ljubljana, Slovenia;1. National Facility for High Field NMR, Tata Institute of Fundamental Research, Homi Bhabha Road, Mumbai 400005, India;2. Principal K M Kundnani College of Pharmacy, Cuffe Parade, Mumbai 400005, India;1. School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan;2. Tokai University Institute of Innovative Science and Technology, 4-1-1, Kitakaname, Hiratsuka-city, Kanagawa 259-1292, Japan |
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| Abstract: | Deracemization of (±)-3-hydroxy-4-chromanone 2 through stereoselective bioreduction to the corresponding (3R,4S)-3,4-chromanediol 3, with good to excellent enantiomeric excesses (up to 99%), mediated by resting cells of the yeast Trichosporon cutaneum CCT 1903, is reported. In addition, 3-hydroxychromone (7) was obtained as a secondary product. |
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