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Molecules 2017, 22(9), 1523; doi:10.3390/molecules22091523

Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens

1
State Key Laboratory of Bioreactor Engineering, Newworld Institute of Biotechnology, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
2
Research Laboratory for Functional Nanomaterial, National Engineering Research Center for Nanotechnology, Shanghai 200241, China
3
Department of Pathology, Microbiology and Immunology, School of medicine, University of South Carolina, 6311 Garners Ferry Rd., Columbia, SC 29209, USA
*
Authors to whom correspondence should be addressed.
Received: 24 July 2017 / Revised: 27 August 2017 / Accepted: 4 September 2017 / Published: 19 September 2017
(This article belongs to the Special Issue Lipases and Lipases Modification)
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Abstract

This work presents a synthetic route to produce chloramphenicol esters by taking advantage the high enantio- and regio-selectivity of lipases. A series of chloramphenicol esters were synthesized using chloramphenicol, acyl donors of different carbon chain length and lipase LipBA (lipase cloned from Bacillus amyloliquefaciens). Among acyl donors with different carbon chain lengths, vinyl propionate was found to be the best. The influences of different organic solvents, reaction temperature, reaction time, enzyme loading and water content on the synthesis of the chloramphenicol esters were studied. The synthesis of chloramphenicol propionate (0.25 M) with 4.0 g L−1 of LipBA loading gave a conversion of ~98% and a purity of ~99% within 8 h at 50 °C in 1,4-dioxane as solvent. The optimum mole ratio of vinyl propionate to chloramphenicol was increased to 5:1. This is the first report of B. amyloliquefaciens lipase being used in chloramphenicol ester synthesis and a detailed study of the synthesis of chloramphenicol propionate using this reaction. The high enzyme activity and selectivity make lipase LipBA an attractive catalyst for green chemical synthesis of molecules with complex structures. View Full-Text
Keywords: enzymatic catalysis; regioselectivity; chloramphenicol esters; green chemistry; Bacillus amyloliquefaciens enzymatic catalysis; regioselectivity; chloramphenicol esters; green chemistry; Bacillus amyloliquefaciens
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Dong, F.; Li, L.; Lin, L.; He, D.; Chen, J.; Wei, W.; Wei, D. Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens. Molecules 2017, 22, 1523.

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