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Molecules 2012, 17(12), 13813-13824; doi:10.3390/molecules171213813
Article

Lipases as Tools in the Synthesis of Prodrugs from Racemic 9-(2,3-Dihydroxypropyl)adenine

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Received: 17 September 2012 / Revised: 15 November 2012 / Accepted: 16 November 2012 / Published: 22 November 2012
(This article belongs to the Special Issue Biocatalysis and Biotransformations in Organic Synthesis)
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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 lipase; transesterification; prodrug; immobilization of enzymes
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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