16255-46-2Relevant academic research and scientific papers
Synthesis of Ester Derivatives of Chloramphenicol by Lipase-Catalyzed Transesterification in Organic Solvents
Ottolina, Gianluca,Carrea, Giacomo,Riva, Sergio
, p. 2366 - 2369 (1990)
Regioselective esterification of chloramphenicol (1) and its synthetic analogue thiamphenicol (2) has been achieved by the action of lipase in acetone and several methyl carboxylates.Aliphatic and aromatic esters of different sizes and natures have been introduced selectively on the primary hydroxyl group of these molecules by modification of the reaction conditions (e.g., temperature, solvent, and lipase source).
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
, (2017/09/25)
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.
Enzymatic regioselective production of chloramphenicol esters
Bizerra, Ayla M.C.,Montenegro, Tasso G.C.,Lemos, Telma L.G.,De Oliveira, Maria C.F.,De Mattos, Marcos C.,Lavandera, Iván,Gotor-Fernández, Vicente,De Gonzalo, Gonzalo,Gotor, Vicente
, p. 2858 - 2862 (2011/05/12)
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.
