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.
Highlights
In recent years, enzymes have been applied to synthesize chloramphenicol derivatives, which has aroused widespread interest because of their high activity, moderate catalytic conditions, and environmental friendliness
Enzymes have been applied to synthesize chloramphenicol derivatives, which has aroused widespread interest because of their high activity, moderate catalytic conditions, and environmental friendliness. This due to the fact that the enzymatic approach avoids the need for protection and deprotection procedures to discriminate between the different available hydroxyl groups in chloramphenicol, as chloramphenicol substituents on the primary hydroxyl group are rapidly hydrolyzed in vivo to the biologically active drug [1]
Enzymatic catalysis with its high enantio- and regioselectivity is attractive for the green synthesis of chemical compounds
Summary
Enzymes have been applied to synthesize chloramphenicol derivatives, which has aroused widespread interest because of their high activity, moderate catalytic conditions, and environmental friendliness. This due to the fact that the enzymatic approach avoids the need for protection and deprotection procedures to discriminate between the different available hydroxyl groups in chloramphenicol, as chloramphenicol substituents on the primary hydroxyl group are rapidly hydrolyzed in vivo to the biologically active drug [1]. The separation steps to remove impurities that have close physical and chemical properties to the target compound results in lower final conversion, higher costs, time-and energy-consumption and excess discharge of waste In this sense, enzymatic catalysis with its high enantio- and regioselectivity is attractive for the green synthesis of chemical compounds. Bizerra et al reported that the Candida antarctica lipase type B (CAL-B)
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