Open AccessPreparation of methyl ester precursors of biologically active agents
Author(s) -
Yunfan Zou,
Marcela Rojas-Pierce,
Natasha V. Raikhel,
Michael C. Pirrung
Publication year - 2008
Publication title -
biotechniques/biotechniques
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.617
H-Index - 131
eISSN - 1940-9818
pISSN - 0736-6205
DOI - 10.2144/000112704
Subject(s) - methyl iodide , salt (chemistry) , chemistry , ion exchange resin , biological activity , organic chemistry , membrane , iodide , elution , carboxylic acid , chromatography , combinatorial chemistry , biochemistry , in vitro
This method enables scientists to easily convert biologically active carboxylic acids into their methyl esters ("pro-drugs" generally having improved ability to penetrate cell membranes) using only equipment commonly found in a biology laboratory. An ion-exchange resin is used to convert the acid into its salt, which is thereby sequestered on the resin. The addition of methyl iodide converts the salt to the ester, which has no affinity for the resin and is readily eluted. Evaporation of the liquid phase provides the pure methyl ester. The preparation in good chemical yields of methyl esters of bioactive agents in excellent purity and 10–20 mg quantities can be achieved using this method. The method can be completed in 1 day.