Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone

被引：19
|
作者：
Quintana, Paula G.
Baldessari, Alicia [1 ]
机构：
[1] Univ Buenos Aires, Lab Biocatalisis, Dept Quim Organ, Buenos Aires, DF, Argentina
来源：
STEROIDS | 2009年 / 74卷 / 13-14期
关键词：
Hydrocortisone fatty acid esters; Lipase-catalyzed reactions; DEACETYLATION; DERIVATIVES; KERATINOCYTES; ANDROSTANE; ACYLATION; STEROIDS; CORTISOL;
D O I：
10.1016/j.steroids.2009.07.010
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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. (C) 2009 Elsevier Inc. All rights reserved.
引用
收藏
页码：1007 / 1014
页数：8
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