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.
Steroids. 2009 Nov-Dec;74(13-14):1007-14. doi: 10.1016/j.steroids.2009.07.010. Epub 2009 Aug 7.
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.
已通过酶法制备了一系列氢化可的松的脂肪酸衍生物。通过脂肪酶催化的酯化、酯交换和醇解反应，以高度区域选择性的方式获得了 9 种 21-单酰基产物和 1 种 3,11,17-三乙酰基衍生物，其中 9 种为新化合物。评估了各种反应参数的影响，如酰化剂：底物比、酶：底物比、溶剂、温度和酰化剂和醇的性质。在测试的脂肪酶中，南极假丝酵母脂肪酶似乎是最合适的，尤其是在一锅法酯交换中表现出高效的行为。该方法具有反应条件温和、环境影响低等优点，使生物催化成为制备氢化可的松酰基衍生物的一种便捷方式。这些亲脂性化合物是制药行业的潜在产品。
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