Enantioseparation of chiral ofloxacin using biomacromolecules

Wei Li; Yanli Li; Yan Fu; Jinli Zhang

Korean Journal of Chemical Engineering, Vol.30, No.7, 1448-1453, July, 2013

DOI10.1007/s11814-013-0048-1 Export Citation

Enantioseparation of chiral ofloxacin using biomacromolecules

Wei Li^†, Yanli Li, Yan Fu, and Jinli Zhang

Key Laboratory for Green Chemical Technology MOE, Key Laboratory of Systems Bioengineering MOE, Tianjin University, Tianjin 300072, P. R. China

E-mail:

Natural biomacromolecules including bovine serum albumin (BSA), calf thymus DNA (ct-DNA) and fish sperm DNA (fs-DNA) were studied as the free chiral selectors to separate R- and S-ofloxacin enantiomers from racemic ofloxacin, combined with ultrafiltration and subsequent crystallization. First, the interactions between chiral ofloxacin and biomacromolecules including BSA, ct-DNA, and fs-DNA were investigated using circular dichroism and fluorescence spectroscopy. BSA exhibited stereoselective adsorption towards R-ofloxacin at pH 9.0 with an enantioselectivity of 1.23, while ct-DNA showed enantiospecific interaction with S-enantiomer with the selectivity of 1.70 at pH 5.0. One single-stage adsorption by BSA provides an enantiomeric excess in the permeate (e.e.p) of 14% in S-enantiomer, and five-stage operations enhance the chiral resolution to reach the e.e.p value of 44%. R-enantiomer with an e.e.p of -26% can be obtained through one single-stage adsorption by using ct-DNA, and -85% can be reached by five-stage operations. Enantiomeric mixtures with the intial e.e. of 44% (S-) can be upgraded to 95% (S-) through subsequent crystallization. This programmable process of adsorption and desorption using BSA or ct-DNA as chiral selectors can be successfully applied to produce the enantiomers with highly optical purity.

Keywords:Enantioseparation Bovine Serum Albumin DNA Chiral Drug Ofloxacin

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[Referenced By]

[1] Maier NM, Franco P, Lindner W, J. Chromatogr. A., 906, 3 (2001)

[2] Sheldon RA, Chirotechnology: Industrial synthesis of optically active compounds, Marcel. Dekker. Inc., New York (1993)

[3] Thomas C, Top 10 biggest-selling prescription drugs, http://ethicalnag. org/2011/05/15/drug-costs-consumer-reports.

[4] Srisanga S, ter Horst JH, Cryst. Growth. Des., 10, 1808 (2010)

[5] Ward TJ, Ward KD, Anal. Chem., 84, 626 (2012)

[6] Ma C, Xu XL, Ai P, Xie SM, Lv YC, Shan HQ, Yuan LM, Chirality., 23, 379 (2011)

[7] Ul-Haq N, Khan T, Park JK, J. Chem. Technol. Biotechnol., 83(4), 524 (2008)

[8] Tang KW, Zhang PL, Pan CY, Li HJ, AIChE J., 57(11), 3027 (2011)

[9] Steensma M, Kuipers NJ, de Haan AB, Kwant G, J. Chem. Technol. Biotechnol., 81(4), 588 (2006)

[10] Sekhon BS, Int. J. ChemTech Res., 2, 1584 (2010)

[11] Jiang JB, Song KS, Chen Z, Zhou Q, Tang YW, Gu FL, Zuo XJ, Xu ZG, J. Chromatogr. A., 1218, 3763 (2011)

[12] Edwie F, Li Y, Chung TS, J. Membr. Sci., 362(1-2), 501 (2010)

[13] Wang HL, Li Y, Chung TS, AIChE J., 55(9), 2284 (2009)

[14] Zhang LJ, Song MF, Tian Q, Min SG, Sep. Purif. Technol., 55(3), 388 (2007)

[15] Higuchi A, Hashimoto T, Yonehara M, Kubota N, Watanabe K, Uemiya S, Kojima T, Hara M, J. Membr. Sci., 130(1-2), 31 (1997)

[16] Higuchi A, Yomogita H, Yoon BO, Kojima T, Hara M, Maniwa S, Saitoh M, J. Membr. Sci., 205(1-2), 203 (2002)

[17] Higuchi A, Higuchi Y, Furuta K, Yoon BO, Hara M, Maniwa S, Saitoh M, Sanui K, J. Membr. Sci., 221(1-2), 207 (2003)

[18] Iritani E, Katagiri N, Kawabata T, Takaishi Y, Sep. Purif. Technol., 64(3), 337 (2009)

[19] Fu Y, Huang TT, Chen B, Shen J, Duan XL, Zhang JL, Li W, Sep. Purif. Thechnol., 107, 11 (2013)

[20] Hayakawa I, Atarashi S, Yokohama S, Imamura M, Sakano K, Furukawa M, Antimicrob. Agents. Chemother., 29, 163 (1986)

[21] Drew RH, Gallis HA, Pharmacotherapy., 8, 35 (1988)

[22] Kumar CV, Asuncion EH, J. Am. Chem. Soc., 115, 8547 (1993)

[23] Yu CH, Al-Saadi A, Shih SJ, Qiu L, Tam KY, Tsang SC, J. Phys. Chem. C., 113, 537 (2009)

[24] Chuang VTG, Otagiri M, Chirality., 18, 159 (2006)

[25] Bertucci C, Canepa A, Ascoli GA, Guimaraes LFL, Felix G, Chirality., 11, 675 (1999)

[26] Al-Rawashdeh NAF, Azzam W, Res. Chem. Intermediat., 37, 759 (2011)

[27] Itoh T, Saura Y, Tsuda Y, Yamada H, Chirality., 9, 643 (1997)

[28] Zhu XF, Ding YS, Lin BC, Jakob A, Koppenhoefer B, Electrophoresis., 20, 1869 (1999)

[29] Son GS, Yeo JA, Kim MS, Kim SK, Holmen A, Akerman B, Norden B, J. Am. Chem. Soc., 120(26), 6451 (1998)

[30] Bailly C, Colson P, Houssier C, Biophys. Res. Commun., 243, 844 (1998)

[31] Keurentjes JT, Nabuurs LJ, Vegter EA, J. Membr. Sci., 113(2), 351 (1996)

[32] Wurges K, Petrusevska-Seebach K, Elsner MP, Lutz S, Biotechnol. Bioeng., 104(6), 1235 (2009)

[33] Gou LZ, Robl S, Leonhard K, Lorenz H, Sordo M, Butka A, Kesselheim S, Wolff M, Seidel-Morgenstern A, Schaber K, Chirality., 23, 118 (2011)

[34] Svang-Ariyaskul A, Koros WJ, Rousseau RW, Chem. Eng.Sci., 77, 35 (2012)