Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate

The enzymatic regioselective monopalmitoylation of racemic 9-(2,3-dihydroxypropyl)- adenine (DHPA), an approved antiviral agent, has been performed by an immobilized form of Candida antarctica B lipase (CAL-B) using a 4:1 DMF/hexane mixture as the reaction medium. To improve the chemical yield of th...

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Bibliographic Details
Published in:Molecules
Main Authors: Brabcová, Jana, Blazek, J., Krecmerová, Marcela, Vondrášek, Jiří, Palomo, José Miguel, Zarevúcka, Marie
Other Authors: Fundación Ramón Areces, Academy of Sciences of the Czech Republic, Consejo Superior de Investigaciones Científicas (España)
Format: Article in Journal/Newspaper
Language:unknown
Published: Multidisciplinary Digital Publishing Institute 2016
Subjects:
Antarc*
Antarctica
Online Access:http://hdl.handle.net/10261/149218
https://doi.org/10.3390/molecules21050648
https://doi.org/10.13039/100008054
https://doi.org/10.13039/501100003339
https://doi.org/10.13039/501100004240
Description
Summary:The enzymatic regioselective monopalmitoylation of racemic 9-(2,3-dihydroxypropyl)- adenine (DHPA), an approved antiviral agent, has been performed by an immobilized form of Candida antarctica B lipase (CAL-B) using a 4:1 DMF/hexane mixture as the reaction medium. To improve the chemical yield of the desired monopalmitoylation reaction, solid-phase chemical modifications of the lipase were evaluated. The reaction yield was successfully increased obtaining 100% product after a second treatment of the product solution with fresh immobilised chemically glycosylated-CAL-B. The authors thank the Ramon Areces Foundation for financial support and the Academy of Sciences of the Czech Republic (project No. M200551203). The authors are grateful to the team of Jan Balzarini at the Rega Institute for Medical Research KU Leuven (Belgium) for the screening of biological activity and thank Abian from the Institute for Biocomputation and Physics (BIFI) for technical support in the CD and fluorescent spectra as well as Ramiro Martinez from Novozymes for the generous gift of lipases. We thank Lydia Burke (Technical Dublin University, Irland) for the proof-reading of the article We acknowledge support by the CSIC Open Access Publication Initiative through its Unit of Information Resources for Research (URICI).

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