Enzymatic regioselective production of chloramphenicol esters

TETRAHEDRON

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Article

Bizerra, Ayla M. C.^1,2  Montenegro, Tasso G. C.^1,2  Lemos, Telma L. G.¹  de Oliveira, Maria C. F.¹  de Mattos, Marcos C.¹  Lavandera, Ivan²  Gotor-Fernandez, Vicente²  de Gonzalo, Gonzalo²  Gotor, Vicente² 

[1] Univ Fed Ceara, Dept Quim Organ & Inorgan, BR-60451970 Fortaleza, Ceara, Brazil

[2] Univ Oviedo, Inst Univ Biotecnol Asturias, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain

关键词: Biocatalysis;    Chloramphenicol;    Lipases;    Regioselective processes;    Medium engineering;   

DOI  :  10.1016/j.tet.2011.02.070

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

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