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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Published in:Molecules
Main Authors: Jana Brabcová, Jiří Blažek, Marcela Krečmerová, Jiří Vondrášek, Jose M. Palomo, Marie Zarevúcka
Format: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2016
Subjects:
regioselectivity
palmitoylation
glycosylation
chemical modification
Organic chemistry
QD241-441
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/molecules21050648
https://doaj.org/article/49fe1fa435644b4faf621b6d114d52a9
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spelling ftdoajarticles:oai:doaj.org/article:49fe1fa435644b4faf621b6d114d52a9 2023-05-15T13:30:40+02:00 Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate Jana Brabcová Jiří Blažek Marcela Krečmerová Jiří Vondrášek Jose M. Palomo Marie Zarevúcka 2016-05-01T00:00:00Z https://doi.org/10.3390/molecules21050648 https://doaj.org/article/49fe1fa435644b4faf621b6d114d52a9 EN eng MDPI AG http://www.mdpi.com/1420-3049/21/5/648 https://doaj.org/toc/1420-3049 1420-3049 doi:10.3390/molecules21050648 https://doaj.org/article/49fe1fa435644b4faf621b6d114d52a9 Molecules, Vol 21, Iss 5, p 648 (2016) regioselectivity palmitoylation glycosylation chemical modification Organic chemistry QD241-441 article 2016 ftdoajarticles https://doi.org/10.3390/molecules21050648 2022-12-31T11:50:21Z 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. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Molecules 21 5 648
institution Open Polar
collection Directory of Open Access Journals: DOAJ Articles
op_collection_id ftdoajarticles
language English
topic regioselectivity
palmitoylation
glycosylation
chemical modification
Organic chemistry
QD241-441
spellingShingle regioselectivity
palmitoylation
glycosylation
chemical modification
Organic chemistry
QD241-441
Jana Brabcová
Jiří Blažek
Marcela Krečmerová
Jiří Vondrášek
Jose M. Palomo
Marie Zarevúcka
Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate
topic_facet regioselectivity
palmitoylation
glycosylation
chemical modification
Organic chemistry
QD241-441
description 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.
format Article in Journal/Newspaper
author Jana Brabcová
Jiří Blažek
Marcela Krečmerová
Jiří Vondrášek
Jose M. Palomo
Marie Zarevúcka
author_facet Jana Brabcová
Jiří Blažek
Marcela Krečmerová
Jiří Vondrášek
Jose M. Palomo
Marie Zarevúcka
author_sort Jana Brabcová
title Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate
title_short Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate
title_full Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate
title_fullStr Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate
title_full_unstemmed Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate
title_sort regioselective palmitoylation of 9-(2,3-dihydroxy- propyl)adenine catalyzed by a glycopolymer-enzyme conjugate
publisher MDPI AG
publishDate 2016
url https://doi.org/10.3390/molecules21050648
https://doaj.org/article/49fe1fa435644b4faf621b6d114d52a9
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_source Molecules, Vol 21, Iss 5, p 648 (2016)
op_relation http://www.mdpi.com/1420-3049/21/5/648
https://doaj.org/toc/1420-3049
1420-3049
doi:10.3390/molecules21050648
https://doaj.org/article/49fe1fa435644b4faf621b6d114d52a9
op_doi https://doi.org/10.3390/molecules21050648
container_title Molecules
container_volume 21
container_issue 5
container_start_page 648
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