Preparation of (R)- and (S)-4-chloro-3-acetoxybutyronitrile using microbial resolution |
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| Institution: | 1. Medicine School, Physiotherapy Department, Federal University of Ceara, Fortaleza, Ceara, Brazil;2. Brasil University, Postgraduate program in Biomedical Engineering, Brazil;3. Medicine Department, Federal University of São Carlos, São Paulo, Brazil;4. Brazilian Enterprise of Agriculture Research, EMBRAPA, São Carlos, SP, Brazil;5. Biotechnology Department, Federal University of São Carlos, São Paulo, Brazil;6. Nove de Julho University (UNINOVE), Bauru, SP, Brazil;7. Wellman Center for Photomedicine, Massachusetts General Hospital, Boston, MA 02114, USA;8. Department of Dermatology, Harvard Medical School, Boston, MA 02115, USA;9. Harvard-MIT Division of Health Sciences and Technology, Cambridge, MA 02139, USA;10. Physiotherapy Department, Federal University of Sao Carlos, Sao Paulo, Brazil;1. Central Laboratories for Key Technologies, Kirin Co. Ltd., Yokohama, Japan;2. Technical Deveropment Center, Koiwai Dairy Products Co Ltd., Sayama, Japan |
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| Abstract: | A new preparation of optically active 4-chloro-3-acetoxybutyronitrile (AcBN) was developed using the resting cells of bacteria. The resolution was based on enantioselective hydrolysis of the ester function of the substrate. (R)-AcBN was prepared using Pseudomonas sp. DS-K-717, and the resulting (R)-AcBN was obtained with high enantiomeric excess of >98% with a yield of 36% during the microbial resolution step. (S)-AcBN was prepared in the same manner using the resting cells of Pseudomonas sp. DS-K-19 and showed a high enantiomeric excess of >98% with a yield of 32%. The enzyme activity was enhanced and induced by the addition of AcBN, particularly the (R)-ester hydrolysis, which was enhanced 20-fold. |
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