Deracemisation of aromatic β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 and determination of absolute configuration by 1H NMR |
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| Institution: | 1. Departamento de Ingeniería Química, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain;2. University of California-Davis, Olive Center, Davis, CA 95616, United States;1. Department of Pathophysiology, Shanghai Universities E-Institute for Chemical Biology, Key Laboratory of Cell Differentiation and Apoptosis of the Chinese Ministry of Education, Shanghai Jiao Tong University School of Medicine, 227 South Chongqing Road, Shanghai 200025, PR China;2. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, PR China;1. Department of Neurology, Prasat Neurological Institute, Bangkok, Thailand;2. Department of Medicine, Nopparat Ratchathani Hospital, Bangkok, Thailand;1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, 119991, Moscow, Russia;2. Faculty of Science, RUDN University, 6 Miklukho-Maklaya St, Moscow 117198, Russian Federation;3. National Research Center “Kurchatov Institute”, pl. Akad. Kurchatova, 1, 123098 Moscow, Russia;1. Infectious Diseases Research Laboratory, 4th Dept. of Internal Medicine, National and Kapodistrian University of Athens, Medical School, “Attikon” University Hospital, Athens, Greece;2. 2nd Department of Pathology, National and Kapodistrian University of Athens, Medical School, “Attikon” University Hospital, Athens, Greece |
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| Abstract: | Deracemisation of aryl and substituted aryl β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 yields the corresponding (S)-enantiomer in >99% enantiomeric excess and good yield (up to 68%). The absolute configuration of ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate and ethyl 3-hydroxy-5-phenyl-pent-4-enoate as determined by 1H NMR using MTPA chloride was found to be ‘S’. The chemical shifts of the methoxy groups of the two diastereomeric MTPA esters were used as diagnostic signals to determine the absolute configuration. |
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