Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone.
A series of fatty acid derivatives of hydrocortisone has been prepared by an enzymatic methodology. Nine 21-monoacyl products and one 3,11,17-triacetyl derivative, nine of them novel compounds, were obtained in a highly regioselective way through lipase-catalyzed esterification, transesterification and alcoholysis reactions. The influence of various reaction parameters such as acylating agent: substrate ratio, enzyme: substrate ratio, solvent, temperature and nature of acylating agent and alcohol was evaluated. Among the tested lipases, Candida antarctica lipase appeared to be the most appropriate and showed a high efficient behavior especially in a one-pot transesterification. The advantages presented by this methodology, such as mild reaction conditions and low environmental impact, make the biocatalysis a convenient way to prepare acyl derivatives of hydrocortisone. These lipophilic compounds are potential products in the pharmaceutical industry.
Quintana
Paula G
PG
Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Piso 3, Cuidad Universitaria, Buenos Aires, Argentina. pquintana@qo.fcen.uba.ar
Baldessari
Alicia
A
D002175:Candida / Q000737:chemistry / Q000201:enzymology; D004951:Esterification; D005227:Fatty Acids / Q000096:biosynthesis*; D006854:Hydrocortisone / Q000031:analogs & derivatives* / Q000096:biosynthesis*; D008049:Lipase / Q000737:chemistry*
D005227:Fatty Acids; D008049:Lipase; D006854:Hydrocortisone