Chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases
The application of Candida antarctica lipase B as catalyst in the synthesis of two examples of nitrogen polymers is described. Firstly, we report a novel linear polyamidoamine oligomer, obtained by polymerization of ethyl acrylate and N-methyl-1,3-diaminopropane, catalyzed by Candida antarctica lipa...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_10643745_v1835_n_p359_Baldessari |
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todo:paper_10643745_v1835_n_p359_Baldessari2023-10-03T16:01:58Z Chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases Baldessari, A. Liñares, G.G. Aza-Michael addition and aminolysis reactions Lipases Nitrogen polymers Polyamidoamine Poly[N-(2-hydroxyethyl)-β-propylamide-g-polycaprolactone] 1,3 propanediamine acrylic acid ethyl ester lipase B n methyl 1,3 diaminopropane nitrogen oligomer polyamidoamine polycaprolactone polymer polypropylene triacylglycerol lipase unclassified drug acetylation aminolysis aqueous solution biocompatibility Burkholderia cepacia Candida antarctica carbon nuclear magnetic resonance catalyst enzyme synthesis matrix assisted laser desorption ionization time of flight mass spectrometry Michael addition molecular weight nonhuman polymerization proton nuclear magnetic resonance ring opening scanning electron microscopy ultraviolet radiation The application of Candida antarctica lipase B as catalyst in the synthesis of two examples of nitrogen polymers is described. Firstly, we report a novel linear polyamidoamine oligomer, obtained by polymerization of ethyl acrylate and N-methyl-1,3-diaminopropane, catalyzed by Candida antarctica lipase B immobilized on polypropylene. The second part of the chapter describes an efficient route for the synthesis of a novel β-peptoid oligomer with hydroxyalkyl pendant groups in the nitrogen atom, through the polymerization of ethyl N-(2-hydroxyethyl)-β-alaninate catalyzed by Candida antarctica lipase B physically adsorbed within a macroporous poly(methyl methacrylate-co-butyl methacrylate) resin. Moreover, two derivatives of the β-peptoid oligomer were prepared: by acetylation and by grafting polycaprolactone. This last process was performed through ring-opening polymerization of caprolactone from the β-peptoid pendant hydroxyl groups and afforded a brush copolymer. The products were blended with polycaprolactone to make films by solvent casting. The inclusion of the acyl derivatives of the β-peptoid to polycaprolactone affected the morphology of the film yielding micro- and nanostructured patterns. The obtained products showed biomedical applications. © Springer Science+Business Media, LLC, part of Springer Nature 2018. SER info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_10643745_v1835_n_p359_Baldessari |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
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Aza-Michael addition and aminolysis reactions Lipases Nitrogen polymers Polyamidoamine Poly[N-(2-hydroxyethyl)-β-propylamide-g-polycaprolactone] 1,3 propanediamine acrylic acid ethyl ester lipase B n methyl 1,3 diaminopropane nitrogen oligomer polyamidoamine polycaprolactone polymer polypropylene triacylglycerol lipase unclassified drug acetylation aminolysis aqueous solution biocompatibility Burkholderia cepacia Candida antarctica carbon nuclear magnetic resonance catalyst enzyme synthesis matrix assisted laser desorption ionization time of flight mass spectrometry Michael addition molecular weight nonhuman polymerization proton nuclear magnetic resonance ring opening scanning electron microscopy ultraviolet radiation |
| spellingShingle |
Aza-Michael addition and aminolysis reactions Lipases Nitrogen polymers Polyamidoamine Poly[N-(2-hydroxyethyl)-β-propylamide-g-polycaprolactone] 1,3 propanediamine acrylic acid ethyl ester lipase B n methyl 1,3 diaminopropane nitrogen oligomer polyamidoamine polycaprolactone polymer polypropylene triacylglycerol lipase unclassified drug acetylation aminolysis aqueous solution biocompatibility Burkholderia cepacia Candida antarctica carbon nuclear magnetic resonance catalyst enzyme synthesis matrix assisted laser desorption ionization time of flight mass spectrometry Michael addition molecular weight nonhuman polymerization proton nuclear magnetic resonance ring opening scanning electron microscopy ultraviolet radiation Baldessari, A. Liñares, G.G. Chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases |
| topic_facet |
Aza-Michael addition and aminolysis reactions Lipases Nitrogen polymers Polyamidoamine Poly[N-(2-hydroxyethyl)-β-propylamide-g-polycaprolactone] 1,3 propanediamine acrylic acid ethyl ester lipase B n methyl 1,3 diaminopropane nitrogen oligomer polyamidoamine polycaprolactone polymer polypropylene triacylglycerol lipase unclassified drug acetylation aminolysis aqueous solution biocompatibility Burkholderia cepacia Candida antarctica carbon nuclear magnetic resonance catalyst enzyme synthesis matrix assisted laser desorption ionization time of flight mass spectrometry Michael addition molecular weight nonhuman polymerization proton nuclear magnetic resonance ring opening scanning electron microscopy ultraviolet radiation |
| description |
The application of Candida antarctica lipase B as catalyst in the synthesis of two examples of nitrogen polymers is described. Firstly, we report a novel linear polyamidoamine oligomer, obtained by polymerization of ethyl acrylate and N-methyl-1,3-diaminopropane, catalyzed by Candida antarctica lipase B immobilized on polypropylene. The second part of the chapter describes an efficient route for the synthesis of a novel β-peptoid oligomer with hydroxyalkyl pendant groups in the nitrogen atom, through the polymerization of ethyl N-(2-hydroxyethyl)-β-alaninate catalyzed by Candida antarctica lipase B physically adsorbed within a macroporous poly(methyl methacrylate-co-butyl methacrylate) resin. Moreover, two derivatives of the β-peptoid oligomer were prepared: by acetylation and by grafting polycaprolactone. This last process was performed through ring-opening polymerization of caprolactone from the β-peptoid pendant hydroxyl groups and afforded a brush copolymer. The products were blended with polycaprolactone to make films by solvent casting. The inclusion of the acyl derivatives of the β-peptoid to polycaprolactone affected the morphology of the film yielding micro- and nanostructured patterns. The obtained products showed biomedical applications. © Springer Science+Business Media, LLC, part of Springer Nature 2018. |
| format |
SER |
| author |
Baldessari, A. Liñares, G.G. |
| author_facet |
Baldessari, A. Liñares, G.G. |
| author_sort |
Baldessari, A. |
| title |
Chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases |
| title_short |
Chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases |
| title_full |
Chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases |
| title_fullStr |
Chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases |
| title_full_unstemmed |
Chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases |
| title_sort |
chemoenzymatic synthesis of nitrogen polymers with biomedical applications catalyzed by lipases |
| url |
http://hdl.handle.net/20.500.12110/paper_10643745_v1835_n_p359_Baldessari |
| work_keys_str_mv |
AT baldessaria chemoenzymaticsynthesisofnitrogenpolymerswithbiomedicalapplicationscatalyzedbylipases AT linaresgg chemoenzymaticsynthesisofnitrogenpolymerswithbiomedicalapplicationscatalyzedbylipases |
| _version_ |
1807324253253533696 |