Regioselective enzymatic synthesis of estradiol 17-fatty acid esters

被引：8
|
作者：
Rustoy, EM
Arias, IER
Baldessari, A [1 ]
机构：
[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, Cuidad Univ, Pabellon 2,Piso 3, RA-1428 Buenos Aires, DF, Argentina
[2] Univ Buenos Aires, Fac Ciencias Exactas & Nat, UMYMFOR, Cuidad Univ, RA-1428 Buenos Aires, DF, Argentina
来源：
ARKIVOC | 2005年
关键词：
lipases; enzymatic acylation and alcoholysis; 3,17-beta-estradiol esters;
D O I：
10.3998/ark.5550190.0006.c12
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of acyl esters of 3,17-beta-estradiol has been prepared by an enzymatic methodology. Eleven 17-monoacyl products (five novel compounds) were obtained in a highly regioselective way by acylation of 3,17-beta-estradiol or by alcoholysis of the corresponding diacyl derivatives. The influence of various reaction parameters such as molar ratio, enzyme: substrate ratio and temperature was evaluated. Among the tested lipases, Candida rugosa lipase appeared to be the most appropriate in monoacylation and lipase from Candida antarctica in alcoholysis. The advantages presented by this methodology such as mild reaction conditions, economy and low environmental impact, make the biocatalysis a convenient way to prepare monoacyl derivatives of 3,17-beta-estradiol containing the aromatic 3-hydroxyl group free. Some of these compounds are recongnized as useful products in the pharmaceutical industry.
引用
收藏
页码：175 / 188
页数：14
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