화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Korean Journal of Chemical Engineering, Vol.30, No.1, 166-171, January, 2013
DOI10.1007/s11814-012-0093-1  Export Citation
Bioconversion process for synthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate using liquid-core immobilized Saccharomyces cerevisiae CGMCC No 2233
Sun Xingyuan, Shi Hanbing, Bi Hongxia†, and Ou Zhimin1, †
  • The Third Affiliated Hospital of Qiqihar Medical College, Qiqihar, Heilongjiang 161000, China
  • 1Pharmaceuticals College, Zhejiang University of Technology, Hang Zhou, Zhejiang 310014, China
E-mail:,
Tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate was synthesized using asymmetric reduction of tertbutyl (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 ℃. 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.
Keywords:Asymmetric Reduction;Tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate;Liquid-core Immobilized Cells
  1. Sirtori CR, Pharmacology & Therapeutics., 60, 431 (1993)
  2. Illingworth DR, Bacon S, Am. J. Cardiol., 60, 33G (1987)
  3. Wolberg M, Hummel W, Muller M, Chem. Eur. J., 7, 4562 (2001)
  4. Pfruender H, Amidjojo M, Hang F, Weuster-Botz D, Appl. Microbiol. Biotechnol., 67(5), 619 (2005)
  5. Amidjojo M, Franco-Lara E, Nowak A, Link H, Weuster-Botz D, Appl. Microbiol. Biotechnol., 69(1), 9 (2005)
  6. Haberland J, Kriegesmann A, Wolfram E, Hummel W, Liese A, Appl. Microbiol. Biotechnol., 58(5), 595 (2002)
  7. Kizaki N, Yamada Y, Yasohara Y, Hasegawa J, US Patent, 6,645,746 (2003)
  8. Sun F, Xu G, Wu J, Yang L, Tetrahedron: Asymmetr., 18, 2454 (2007)
  9. Wang P, Cai JB, Ouyang Q, He JY, Su HZ, Appl. Microbiol. Biotechnol., 90(6), 1897 (2011)
  10. Kratzer R, Pukl M, Egger S, Vogl M, Brecker L, Nidetzky B, Biotechnol. Bioeng., 108(4), 797 (2011)
  11. Yu MA, Wei YM, Zhao L, Jiang L, Zhu XB, Qi W, J. Ind.Microbiol. Biotechnol., 34, 151 (2007)
  12. Katz M, Frejd T, Hahn-Hagerdal B, Gorwa-Grausland MF, Biotechnol. Bioeng., 84(5), 573 (2003)
  13. Xie Q, Wu JP, Xu G, Yang LR, Biotechnol. Prog., 22(5), 1301 (2006)
  14. Soni P, Banerjee UC, Biotechnol. J., 1, 80 (2006)
  15. Rocha LC, Ferreira HV, Pimenta EF, Berlinck RGS, Seleghim MHR, Javaroti DCD, Sette LD, Bonugli RC, Porto ALM, Biotechnol. Lett., 31(10), 1559 (2009)
  16. Ou Z, Wu J, Yang L, Cen P, Korean J. Chem. Eng., 25(1), 124 (2008)
  17. Chen BY, Yen CY, Chen WM, Chang CT, Wang CT, Hu YC, Bioresour. Technol., 100(23), 5763 (2009)
  18. BENITO GG, OZORES M, PENA M, Bioresour. Technol., 49(3), 209 (1994)
  19. Li GY, Huang KL, Jiang YR, Ding P, Process Biochem., 42, 1465 (2007)
  20. Xue WM, Yu WT, Liu XD, He X, Wang W, Ma XJ, Chem. J. Chinese U., 25, 1342 (2004)