Articles & Issues
- Language
- English
- Conflict of Interest
- In relation to this article, we declare that there is no conflict of interest.
- Publication history
-
Received March 15, 2012
Accepted June 16, 2012
-
This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits
unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
Copyright © KIChE. All rights reserved.
All issues
Bioconversion process for synthesis of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate using liquid-core immobilized Saccharomyces cerevisiae CGMCC No 2233
The Third Affiliated Hospital of Qiqihar Medical College, Qiqihar, Heilongjiang 161000, China 1Pharmaceuticals College, Zhejiang University of Technology, Hang Zhou, Zhejiang 310014, China
bihongxia20112011@163.com
Korean Journal of Chemical Engineering, January 2013, 30(1), 166-171(6), 10.1007/s11814-012-0093-1
Download PDF
Abstract
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
References
Sirtori CR, Pharmacology & Therapeutics., 60, 431 (1993)
Illingworth DR, Bacon S, Am. J. Cardiol., 60, 33G (1987)
Wolberg M, Hummel W, Muller M, Chem. Eur. J., 7, 4562 (2001)
Pfruender H, Amidjojo M, Hang F, Weuster-Botz D, Appl. Microbiol. Biotechnol., 67(5), 619 (2005)
Amidjojo M, Franco-Lara E, Nowak A, Link H, Weuster-Botz D, Appl. Microbiol. Biotechnol., 69(1), 9 (2005)
Haberland J, Kriegesmann A, Wolfram E, Hummel W, Liese A, Appl. Microbiol. Biotechnol., 58(5), 595 (2002)
Kizaki N, Yamada Y, Yasohara Y, Hasegawa J, US Patent, 6,645,746 (2003)
Sun F, Xu G, Wu J, Yang L, Tetrahedron: Asymmetr., 18, 2454 (2007)
Wang P, Cai JB, Ouyang Q, He JY, Su HZ, Appl. Microbiol. Biotechnol., 90(6), 1897 (2011)
Kratzer R, Pukl M, Egger S, Vogl M, Brecker L, Nidetzky B, Biotechnol. Bioeng., 108(4), 797 (2011)
Yu MA, Wei YM, Zhao L, Jiang L, Zhu XB, Qi W, J. Ind.Microbiol. Biotechnol., 34, 151 (2007)
Katz M, Frejd T, Hahn-Hagerdal B, Gorwa-Grausland MF, Biotechnol. Bioeng., 84(5), 573 (2003)
Xie Q, Wu JP, Xu G, Yang LR, Biotechnol. Prog., 22(5), 1301 (2006)
Soni P, Banerjee UC, Biotechnol. J., 1, 80 (2006)
Rocha LC, Ferreira HV, Pimenta EF, Berlinck RGS, Seleghim MHR, Javaroti DCD, Sette LD, Bonugli RC, Porto ALM, Biotechnol. Lett., 31(10), 1559 (2009)
Ou Z, Wu J, Yang L, Cen P, Korean J. Chem. Eng., 25(1), 124 (2008)
Chen BY, Yen CY, Chen WM, Chang CT, Wang CT, Hu YC, Bioresour. Technol., 100(23), 5763 (2009)
BENITO GG, OZORES M, PENA M, Bioresour. Technol., 49(3), 209 (1994)
Li GY, Huang KL, Jiang YR, Ding P, Process Biochem., 42, 1465 (2007)
Xue WM, Yu WT, Liu XD, He X, Wang W, Ma XJ, Chem. J. Chinese U., 25, 1342 (2004)
Illingworth DR, Bacon S, Am. J. Cardiol., 60, 33G (1987)
Wolberg M, Hummel W, Muller M, Chem. Eur. J., 7, 4562 (2001)
Pfruender H, Amidjojo M, Hang F, Weuster-Botz D, Appl. Microbiol. Biotechnol., 67(5), 619 (2005)
Amidjojo M, Franco-Lara E, Nowak A, Link H, Weuster-Botz D, Appl. Microbiol. Biotechnol., 69(1), 9 (2005)
Haberland J, Kriegesmann A, Wolfram E, Hummel W, Liese A, Appl. Microbiol. Biotechnol., 58(5), 595 (2002)
Kizaki N, Yamada Y, Yasohara Y, Hasegawa J, US Patent, 6,645,746 (2003)
Sun F, Xu G, Wu J, Yang L, Tetrahedron: Asymmetr., 18, 2454 (2007)
Wang P, Cai JB, Ouyang Q, He JY, Su HZ, Appl. Microbiol. Biotechnol., 90(6), 1897 (2011)
Kratzer R, Pukl M, Egger S, Vogl M, Brecker L, Nidetzky B, Biotechnol. Bioeng., 108(4), 797 (2011)
Yu MA, Wei YM, Zhao L, Jiang L, Zhu XB, Qi W, J. Ind.Microbiol. Biotechnol., 34, 151 (2007)
Katz M, Frejd T, Hahn-Hagerdal B, Gorwa-Grausland MF, Biotechnol. Bioeng., 84(5), 573 (2003)
Xie Q, Wu JP, Xu G, Yang LR, Biotechnol. Prog., 22(5), 1301 (2006)
Soni P, Banerjee UC, Biotechnol. J., 1, 80 (2006)
Rocha LC, Ferreira HV, Pimenta EF, Berlinck RGS, Seleghim MHR, Javaroti DCD, Sette LD, Bonugli RC, Porto ALM, Biotechnol. Lett., 31(10), 1559 (2009)
Ou Z, Wu J, Yang L, Cen P, Korean J. Chem. Eng., 25(1), 124 (2008)
Chen BY, Yen CY, Chen WM, Chang CT, Wang CT, Hu YC, Bioresour. Technol., 100(23), 5763 (2009)
BENITO GG, OZORES M, PENA M, Bioresour. Technol., 49(3), 209 (1994)
Li GY, Huang KL, Jiang YR, Ding P, Process Biochem., 42, 1465 (2007)
Xue WM, Yu WT, Liu XD, He X, Wang W, Ma XJ, Chem. J. Chinese U., 25, 1342 (2004)
