Journal
TETRAHEDRON
Volume 67, Issue 16, Pages 2858-2862Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.02.070
Keywords
Biocatalysis; Chloramphenicol; Lipases; Regioselective processes; Medium engineering
Categories
Funding
- CAPES-DGU [149/07]
- CNPq
- FUNCAP
- PRONEX
- Ministerio de Ciencia e Innovacion (MICINN) [CTQ 2007-61126]
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An enzymatic study has been performed in the search for synthetic routes to produce chloramphenicol derivatives through regioselective processes using lipases. Complementary transesterification and hydrolytic reactions have been carried to synthesize chloramphenicol regioisomers. Reaction parameters, such as biocatalyst, solvent, acyl donor, and temperature have been optimised in order to obtain chloramphenicol esters with high yields through acylation processes. Scale-up of the enzymatic reactions (1 g-scale at 0.25 M) and catalyst recycling (up to 10 cycles) have been successfully achieved. Furthermore, monoacylated derivatives at the more hindered secondary position could also be obtained employing hydrolysis processes. (C) 2011 Elsevier Ltd. All rights reserved.
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