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Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens

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 Lip(BA) (lipase cloned fro...

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Autores principales: Dong, Fengying, Li, Lingmeng, Lin, Lin, He, Dannong, Chen, Jingwen, Wei, Wei, Wei, Dongzhi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151736/
https://www.ncbi.nlm.nih.gov/pubmed/28925953
http://dx.doi.org/10.3390/molecules22091523
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author Dong, Fengying
Li, Lingmeng
Lin, Lin
He, Dannong
Chen, Jingwen
Wei, Wei
Wei, Dongzhi
author_facet Dong, Fengying
Li, Lingmeng
Lin, Lin
He, Dannong
Chen, Jingwen
Wei, Wei
Wei, Dongzhi
author_sort Dong, Fengying
collection PubMed
description 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 Lip(BA) (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 Lip(BA) 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 Lip(BA) an attractive catalyst for green chemical synthesis of molecules with complex structures.
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spelling pubmed-61517362018-11-13 Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens Dong, Fengying Li, Lingmeng Lin, Lin He, Dannong Chen, Jingwen Wei, Wei Wei, Dongzhi Molecules Article 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 Lip(BA) (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 Lip(BA) 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 Lip(BA) an attractive catalyst for green chemical synthesis of molecules with complex structures. MDPI 2017-09-19 /pmc/articles/PMC6151736/ /pubmed/28925953 http://dx.doi.org/10.3390/molecules22091523 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Dong, Fengying
Li, Lingmeng
Lin, Lin
He, Dannong
Chen, Jingwen
Wei, Wei
Wei, Dongzhi
Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens
title Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens
title_full Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens
title_fullStr Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens
title_full_unstemmed Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens
title_short Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens
title_sort transesterification synthesis of chloramphenicol esters with the lipase from bacillus amyloliquefaciens
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151736/
https://www.ncbi.nlm.nih.gov/pubmed/28925953
http://dx.doi.org/10.3390/molecules22091523
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