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Preparation of (R)-(−)-mandelic acid and its derivatives from racemates by enantioselective degradation with a newly isolated bacterial strain Alcaligenes sp. ECU0401

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Abstract

An enantioselective mandelate-degrading bacterium, Alcaligenes sp. ECU0401, was newly isolated from soil. By fed-batch culture, (R)-(−)-mandelic acid was successfully prepared in a 5-L fermenter with 32.8% isolated yield and >99.9% enantiomeric excesses (e.e.) from totally 3.04% (w/v) of racemic mandelic acid after 99 h of biotransformation. The optimal reaction pH and temperature were 6.5 and 30 °C, respectively. Using the resting cell as a biocatalyst for asymmetric degradation of racemic mandelic acid and chloro-substituted derivatives thereof, (R)-(−)-mandelic acid, (R)-(−)-o-chloromandelic acid, (S)-(+)-m-chloromandelic acid and (S)-(+)-p-chloromandelic acid were recovered with high analytic yields and excellent enantiomeric excesses (e.e. > 99.9%). (R)-(−)-Mandelic acid could also be obtained after 12 h of biotransformation with 41.5% isolated yield and >99.9% e.e.

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Acknowledgments

This research was financially supported by the National Natural Science Foundation of China (grant no. 20506037) and the Ministry of Education, P. R. China (grant no. 20050251011).

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Authors and Affiliations

  1. Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 200237, Shanghai, People’s Republic of China

    Yu-Cai He, Jian-He Xu, Jiang Pan, Li-Ming Ouyang & Yi Xu

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  1. Yu-Cai He
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  2. Jian-He Xu
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  4. Li-Ming Ouyang
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  5. Yi Xu
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Correspondence to Jian-He Xu.

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He, YC., Xu, JH., Pan, J. et al. Preparation of (R)-(−)-mandelic acid and its derivatives from racemates by enantioselective degradation with a newly isolated bacterial strain Alcaligenes sp. ECU0401. Bioprocess Biosyst Eng 31, 445–451 (2008). https://doi.org/10.1007/s00449-007-0181-5

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  • DOI: https://doi.org/10.1007/s00449-007-0181-5

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