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Lipases as Tools in the Synthesis of Prodrugs from Racemic 9-(2,3-Dihydroxypropyl)adenine
Institute of Chemical Technology Prague, Faculty of Food and Biochemical Technology, Technická 5, 160 28 Prague 6, Czech Republic
Institute of Organic Chemistry and Biochemistry AS CR, Flemingovo n. 2, 166 10 Prague 6, Czech Republic
* Author to whom correspondence should be addressed.
Received: 17 September 2012; in revised form: 15 November 2012 / Accepted: 16 November 2012 / Published: 22 November 2012
Abstract: Lipases from Geotrichum candidum 4013 (extracellular lipase and cell-bound lipase) were immobilized by adsorption on chitosan beads. The enzyme preparations were tested in the synthesis of ester prodrugs from racemic 9-(2,3-dihydroxypropyl)adenine in dimethylformamide with different vinyl esters (acetate, butyrate, decanoate, laurate, palmitate). The transesterification activities of these immobilized enzymes were compared with commercially available lipases (lipase from hog pancreas, Aspergillus niger, Candida antarctica, Pseudomonas fluorescens). Lipase from Candida antarctica was found to be the most efficient enzyme regarding chemical yield of the desired products, while transesterification by lipase from Aspergillus niger resulted in lower yields.
Keywords: lipase; transesterification; prodrug; immobilization of enzymes
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Brabcová, J.; Blažek, J.; Janská, L.; Krečmerová, M.; Zarevúcka, M. Lipases as Tools in the Synthesis of Prodrugs from Racemic 9-(2,3-Dihydroxypropyl)adenine. Molecules 2012, 17, 13813-13824.
Brabcová J, Blažek J, Janská L, Krečmerová M, Zarevúcka M. Lipases as Tools in the Synthesis of Prodrugs from Racemic 9-(2,3-Dihydroxypropyl)adenine. Molecules. 2012; 17(12):13813-13824.
Brabcová, Jana; Blažek, Jiří; Janská, Lucie; Krečmerová, Marcela; Zarevúcka, Marie. 2012. "Lipases as Tools in the Synthesis of Prodrugs from Racemic 9-(2,3-Dihydroxypropyl)adenine." Molecules 17, no. 12: 13813-13824.