Lipase catalyzed enantioselective desymmetrization of a prochiral pentane-1,3,5-triol derivative |
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| Institution: | 1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK;2. AstraZeneca Pharmaceutical Development, Silk Road Business Park, Macclesfield, Cheshire SK10 2NA, UK;1. Department of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido, 090-8507, Japan;2. Laboratory of Metabolism and Biochemistry, Institute of Veterinary Medicine, University of Life Science, Zaisan, Ulaanbaatar, 17024, Mongolia;1. Chemical Biology Unit, Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India;2. CSIR-Institute of Genomics and Integrative Biology, Mall Road, New Delhi 110007, India;1. Department of Chemical Engineering, Annamalai University, Annamalainagar 608002, Tamilnadu, India;2. Department of Chemical Engineering, Sohar University, Sohar, Oman;1. Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano 399-4598, Japan;2. Department of Bioscience and Biotechnology, Faculty of Agriculture, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano 399-4598, Japan;3. Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan;4. Department of Biochemical Engineering, Graduate School of Science and Technology, Yamagata University, Yonezawa, Yamagata 992-8510, Japan |
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| Abstract: | The enantioselective desymmetrization of the prochiral 3-O-silyl protected pentanetriol derivative 3 was carefully investigated. At ?10 °C, the bacterial lipase from Burkholderia cepacia immobilized on ceramic particles led to monoacetate (S)-4 in 52% yield and >99.9% ee. At a reaction temperature of ?40 °C the yield and enantioselectivity were even higher, but the reaction time was very long. Theoretical simulations of the reaction progress indicated an enantioselectivity of 25:1 at ?10 °C and 35:1 at ?40 °C. (S)-4 was converted into the enantiomerically pure building block 5-azidopentane-1,3-diol (S)-7 in two steps. The absolute configuration of (S)-7 was determined by exciton-coupled circular dichroism (ECCD) of diester (S)-8. |
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