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Issue 3, 2016
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Reactive crystallization of β-lactam antibiotics: strategies to enhance productivity and purity of ampicillin

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Abstract

Seeded reactive crystallization in the manufacture of semi-synthetic β-lactam antibiotics is described and the beneficial effects on yield are discussed. Conventional enzymatic synthesis of β-lactam is limited by secondary hydrolysis reactions that consume the desired product as it is being produced. Recent work in this area has pointed to the potential advantage of performing reactions at conditions that allow product crystallization to reduce the rate of secondary hydrolysis by protecting ampicillin in the solid phase. However, these approaches led to crystallization of both D-phenylglycine and ampicillin, which will greatly increase downstream processing. In the work described here, seeded crystallization is used to promote secondary nucleation of the desired ampicillin while it is being produced by the synthesis reaction, thereby selectively crystallizing ampicillin. Quantification of the solid phase confirmed selective crystallization of ampicillin with purities greater than 95% wt in all runs.

Graphical abstract: Reactive crystallization of β-lactam antibiotics: strategies to enhance productivity and purity of ampicillin

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Publication details

The article was received on 14 Dec 2015, accepted on 22 Feb 2016 and first published on 01 Mar 2016


Article type: Paper
DOI: 10.1039/C5RE00092K
React. Chem. Eng., 2016,1, 321-329

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    Reactive crystallization of β-lactam antibiotics: strategies to enhance productivity and purity of ampicillin

    L. G. Encarnación-Gómez, A. S. Bommarius and R. W. Rousseau, React. Chem. Eng., 2016, 1, 321
    DOI: 10.1039/C5RE00092K

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