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Bioconversion process for synthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate using liquid-core immobilized Saccharomyces cerevisiae CGMCC No 2233

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Abstract

Tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate was synthesized using asymmetric reduction of tert-butyl (S)-6-chloro-5-hydroxy-3-oxo-hexanoate with liquid-core immobilized Saccharomyces cerevisiae CGMCC No. 2233. The optimum conditions for preparation of the liquid-core immobilized cells were found to be 2% guar gum, 5% CaCl2, 0.8% sodium alginate, capsule diameter 2mm, 0.3% chitosan (1.0×105) solution, and 30 min for formation of the film of liquid-core immobilized cells. The optimum re-cultivation time was 32 h. The optimum reduction conditions were found to be pH 6.8–7.2, 160 r/min, and 30 °C. Conversion was found to reach 100% when initial concentration of substrate was less than 50 g/L. The diastereomeric excess of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate exceeded 99%. The liquid-core immobilized cells retained their effectiveness even after 15 uses.

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References

  1. C. R. Sirtori, Pharmacology & Therapeutics, 60, 431 (1993).

    Article  CAS  Google Scholar 

  2. D. R. Illingworth and S. Bacon, Am. J. Cardiol., 60, 33G (1987).

    Article  CAS  Google Scholar 

  3. M. Wolberg, W. Hummel and M. Müller, Chem. Eur. J., 7, 4562 (2001).

    Article  CAS  Google Scholar 

  4. H. Pfruender, M. Amidjojo, F. Hang and D. Weuster-Botz, Appl. Microbiol. Biotechnol., 67, 619 (2005).

    Article  CAS  Google Scholar 

  5. M. Amidjojo, E. Franco-Lara, A. Nowak, H. Link and D. Weuster-Botz, Appl. Microbiol. Biotechnol., 69, 9 (2005).

    Article  CAS  Google Scholar 

  6. J. Haberland, A. Kriegesmann, E. Wolfram, W. Hummel and A. Liese, Appl. Microbiol. Biotechnol., 58, 595 (2002).

    Article  CAS  Google Scholar 

  7. N. Kizaki, Y. Yamada, Y. Yasohara and J. Hasegawa, US Patent, 6,645,746 (2003).

  8. F. Sun, G. Xu, J. Wu and L. Yang, Tetrahedron: Asymmetr., 18, 2454 (2007).

    Article  CAS  Google Scholar 

  9. P. Wang, J. B. Cai, Q. Ouyang, J.Y. He and H. Z. Su, Appl. Microbiol. Biotechnol., 90, 1897 (2011).

    Article  CAS  Google Scholar 

  10. R. Kratzer, M. Pukl, S. Egger, M. Vogl, L. Brecker and B. Nidetzky, Biotechnol. Bioeng., 108, 797 (2011).

    Article  CAS  Google Scholar 

  11. M.A. Yu, Y.M. Wei, L. Zhao, L. Jiang, X.B. Zhu and W. Qi, J. Ind. Microbiol. Biotechnol., 34, 151 (2007).

    Article  CAS  Google Scholar 

  12. M. Katz, T. Frejd, B. Hahn-Hägerdal and M. F. Gorwa-Grauslund, Biotechnol. Bioeng., 84, 573 (2003).

    Article  CAS  Google Scholar 

  13. Q. Xie, J. Wu, G. Xu and L. Yang, Biotechnol. Prog., 22, 1301 (2006).

    Article  CAS  Google Scholar 

  14. P. Soni and U. C. Banerjee, Biotechnol. J., 1, 80 (2006).

    Article  CAS  Google Scholar 

  15. L. C. Rocha, H. V. Ferreira, E. F. Pimenta, R. G. Berlinck, M. H. Seleghim, D. C. Javaroti, L. D. Sette, R.C. Bonugli and A. L. Porto, Biotechnol. Lett., 31, 1559 (2009).

    Article  CAS  Google Scholar 

  16. Z. Ou, J. Wu, L. Yang and P. Cen, Korean J. Chem. Eng., 25, 124 (2008).

    Article  CAS  Google Scholar 

  17. B.Y. Chen, C.Y. Yen, W.M. Chen, C. T. Chang, C. T. Wang and Y. C. Hu, Bioresour. Technol., 100, 5763 (2009).

    Article  CAS  Google Scholar 

  18. G. Benito, M. Ozores and M. Peña, Bioresour. Technol., 49, 209 (1994).

    Article  Google Scholar 

  19. G.Y. Li, K. L. Huang, Y. R. Jiang and P. Ding, Process Biochem., 42, 1465 (2007).

    Article  CAS  Google Scholar 

  20. W.M. Xue, W. T. Yu, X. D. Liu, X. He, W. Wang and X. J. Ma, Chem. J. Chinese U., 25, 1342 (2004).

    CAS  Google Scholar 

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Authors and Affiliations

  1. The Third Affiliated Hospital of Qiqihar Medical College, Qiqihar, Heilongjiang, 161000, China

    Sun Xingyuan, Shi Hanbing & Bi Hongxia

  2. Pharmaceuticals College, Zhejiang University of Technology, Hang Zhou, Zhejiang, 310014, China

    Ou Zhimin

Authors
  1. Sun Xingyuan
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  2. Shi Hanbing
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  3. Bi Hongxia
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  4. Ou Zhimin
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Correspondence to Bi Hongxia or Ou Zhimin.

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Xingyuan, S., Hanbing, S., Hongxia, B. et al. Bioconversion process for synthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate using liquid-core immobilized Saccharomyces cerevisiae CGMCC No 2233. Korean J. Chem. Eng. 30, 166–171 (2013). https://doi.org/10.1007/s11814-012-0093-1

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  • DOI: https://doi.org/10.1007/s11814-012-0093-1

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