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Enantioseparation of chiral ofloxacin using biomacromolecules

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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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Authors and Affiliations

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

    Wei Li, Yanli Li, Yan Fu & Jinli Zhang

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  1. Wei Li
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  2. Yanli Li
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  3. Yan Fu
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  4. Jinli Zhang
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Correspondence to Wei Li.

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Li, W., Li, Y., Fu, Y. et al. Enantioseparation of chiral ofloxacin using biomacromolecules. Korean J. Chem. Eng. 30, 1448–1453 (2013). https://doi.org/10.1007/s11814-013-0048-1

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  • DOI: https://doi.org/10.1007/s11814-013-0048-1

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