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Received March 26, 2013
Accepted April 1, 2013
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Enantioseparation of chiral ofloxacin using biomacromolecules
Key Laboratory for Green Chemical Technology MOE, Key Laboratory of Systems Bioengineering MOE, Tianjin University, Tianjin 300072, P. R. China
liwei@tju.edu.cn
Korean Journal of Chemical Engineering, July 2013, 30(7), 1448-1453(6), 10.1007/s11814-013-0048-1
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Abstract
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.
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Bertucci C, Canepa A, Ascoli GA, Guimaraes LFL, Felix G, Chirality., 11, 675 (1999)
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Keurentjes JT, Nabuurs LJ, Vegter EA, J. Membr. Sci., 113(2), 351 (1996)
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