Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde
ilustraciones, fotografías, graficas, tablas
- Autores:
-
Posada rubiano, Nestor camilo
- Tipo de recurso:
- Fecha de publicación:
- 2021
- Institución:
- Universidad Nacional de Colombia
- Repositorio:
- Universidad Nacional de Colombia
- Idioma:
- spa
- OAI Identifier:
- oai:repositorio.unal.edu.co:unal/81524
- Palabra clave:
- 540 - Química y ciencias afines::547 - Química orgánica
POLIMERIZACION DE ABERTURA DE ANILLO
Ring-opening polymerization
Polímeros
Lipasas
Policaprolactona
Curcumina
Biomoléculas
Copolímero
eROP
Curcumin
Biomolecules
Lipases
Polycaprolactone
Copolymer
- Rights
- openAccess
- License
- Atribución-NoComercial-SinDerivadas 4.0 Internacional
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Universidad Nacional de Colombia |
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| dc.title.spa.fl_str_mv |
Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde |
| dc.title.translated.eng.fl_str_mv |
Synthesis of caprolactone polymers by enzymatic ring-opening polymerization implementing lipases as a biocatalytic process with a focus on green chemistry |
| title |
Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde |
| spellingShingle |
Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde 540 - Química y ciencias afines::547 - Química orgánica POLIMERIZACION DE ABERTURA DE ANILLO Ring-opening polymerization Polímeros Lipasas Policaprolactona Curcumina Biomoléculas Copolímero eROP Curcumin Biomolecules Lipases Polycaprolactone Copolymer |
| title_short |
Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde |
| title_full |
Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde |
| title_fullStr |
Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde |
| title_full_unstemmed |
Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde |
| title_sort |
Síntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verde |
| dc.creator.fl_str_mv |
Posada rubiano, Nestor camilo |
| dc.contributor.advisor.none.fl_str_mv |
Pérez Pérez, León Darío |
| dc.contributor.author.none.fl_str_mv |
Posada rubiano, Nestor camilo |
| dc.contributor.researchgroup.spa.fl_str_mv |
Macromoléculas |
| dc.subject.ddc.spa.fl_str_mv |
540 - Química y ciencias afines::547 - Química orgánica |
| topic |
540 - Química y ciencias afines::547 - Química orgánica POLIMERIZACION DE ABERTURA DE ANILLO Ring-opening polymerization Polímeros Lipasas Policaprolactona Curcumina Biomoléculas Copolímero eROP Curcumin Biomolecules Lipases Polycaprolactone Copolymer |
| dc.subject.lemb.spa.fl_str_mv |
POLIMERIZACION DE ABERTURA DE ANILLO |
| dc.subject.lemb.eng.fl_str_mv |
Ring-opening polymerization |
| dc.subject.proposal.spa.fl_str_mv |
Polímeros Lipasas Policaprolactona Curcumina Biomoléculas Copolímero |
| dc.subject.proposal.none.fl_str_mv |
eROP |
| dc.subject.proposal.eng.fl_str_mv |
Curcumin Biomolecules Lipases Polycaprolactone Copolymer |
| description |
ilustraciones, fotografías, graficas, tablas |
| publishDate |
2021 |
| dc.date.issued.none.fl_str_mv |
2021 |
| dc.date.accessioned.none.fl_str_mv |
2022-06-07T16:45:57Z |
| dc.date.available.none.fl_str_mv |
2022-06-07T16:45:57Z |
| dc.type.spa.fl_str_mv |
Trabajo de grado - Maestría |
| dc.type.driver.spa.fl_str_mv |
info:eu-repo/semantics/masterThesis |
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info:eu-repo/semantics/acceptedVersion |
| dc.type.content.spa.fl_str_mv |
Text |
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http://purl.org/redcol/resource_type/TM |
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acceptedVersion |
| dc.identifier.uri.none.fl_str_mv |
https://repositorio.unal.edu.co/handle/unal/81524 |
| dc.identifier.instname.spa.fl_str_mv |
Universidad Nacional de Colombia |
| dc.identifier.reponame.spa.fl_str_mv |
Repositorio Institucional Universidad Nacional de Colombia |
| dc.identifier.repourl.spa.fl_str_mv |
https://repositorio.unal.edu.co/ |
| url |
https://repositorio.unal.edu.co/handle/unal/81524 https://repositorio.unal.edu.co/ |
| identifier_str_mv |
Universidad Nacional de Colombia Repositorio Institucional Universidad Nacional de Colombia |
| dc.language.iso.spa.fl_str_mv |
spa |
| language |
spa |
| dc.relation.references.spa.fl_str_mv |
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Atribución-NoComercial-SinDerivadas 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Pérez Pérez, León Daríoa85c642b1834ea9bb160b576c9ba2f87Posada rubiano, Nestor camiloddb0aa3af0f96cf19dd49b0ce54fa59eMacromoléculas2022-06-07T16:45:57Z2022-06-07T16:45:57Z2021https://repositorio.unal.edu.co/handle/unal/81524Universidad Nacional de ColombiaRepositorio Institucional Universidad Nacional de Colombiahttps://repositorio.unal.edu.co/ilustraciones, fotografías, graficas, tablasEsta investigación está basada en la síntesis de policaprolactona (PCL) y copolímeros de la misma, mediante la polimerización por apertura de anillo incorporando enzimas de tipo lipasa como catalizadores. En principio la síntesis de PCL se ha centrado en la acción de catalizadores químicos y altas demandas experimentales, que se contraponen a la salud ambiental y humana, haciendo evidente que se requieren alternativas que favorezcan la síntesis del poliéster y sus copolímeros, además del cuidado ambiental. Es por ello que se reconoce que la polimerización enzimática por apertura de anillo (eROP) empleando lipasas junto condiciones “suaves” de reacción, constituye la síntesis de copolímeros funcionalizados de PCL como un proceso amigable con el medio ambiente. La eROP a la fecha, aborda aspectos como los tipos de enzimas y su origen, además de los efectos de las condiciones experimentales (solvente, temperatura, iniciadores, etc.) sobre las propiedades del polímero y la estabilidad de las lipasas; es necesario recalcar que dichas exploraciones se centran en polímeros lineales y telequélicos, mientras que se demandan estructuras más versátiles y funcionales, siendo este un campo menos abordado por la polimerización enzimática. Inicialmente se comparó la actividad enzimática sobre la eROP de la caprolactona (ℇ-CL) a partir de dos lipasas con diferente origen y disposición, siendo la primera la lipasa Candida antartica tipo B (CALB) (N-435) y la segunda la lipasa pancreática porcina (PPL). Ambas enzimas en la eROP permitieron la apertura del anillo de ℇ-CL, la PPL evidenció una conversión del 26% y la formación de especies ácidas y oligómeros de tipo dímero y trímero en más de 36 horas de reacción, mientras que la conversión del 100% del monómero fue generado por la N-435 en 4 horas de reacción, con una PCL de alto peso molecular (Mn: 14,1 kDa). En este sentido, la N-435 demostró control de la polimerización y una mejor eficiencia frente la PPL, concordando con la mayor actividad demostrada en la hidrolisis de tri y monoglicéridos. Igualmente, la N-435 en micrografías SEM, exhibe que el soporte de la enzima se ve afectado mecánicamente y puede influir en la reutilización del catalizador. Posteriormente, las condiciones de reacción “suaves” que permitieron la síntesis de PCL con la N-435 y con altos rendimientos en su peso molecular y grados de conversión, fueron establecidas bajo comparación de variaciones en la temperatura, solventes y concentraciones con el catalizador. Se estipuló que la reacción a 70ºC, en tolueno y con una concentración del 10% de N-435 respecto el monómero, permiten el 100% de conversión de la ℇ-CL, buenas propiedades en la PCL y menores exigencias energéticas respecto los catalizadores químicos. Igualmente se señalan los efectos que tiene la variación de la temperatura, solventes y concentraciones, sobre el rendimiento de la reacción, hallando entre estas, alta polidispersión (Ð), disminución de los pesos moleculares y las conversiones. Con el compendio de las condiciones de reacción “suaves” y la alta actividad de la N-435, se obtuvo el copolímero α-azido-ε-caprolactona-co-caprolactona (Poli (α-N3-CL-co-CL)) a dos diferentes pesos moleculares (Mn: 14,7 y 9,5 kDa) y un 100% de conversión, demostrando el control de la N-435 sobre la polimerización. Este copolímero exhibió un comportamiento térmico diferente a la PCL pura, pues la presencia de grupos azida en la cadena de polímero, disminuye las temperaturas de fusión y por ende la cristalización. A causa de este efecto se estima que los cristales del copolímero son de menor tamaño y diferente forma, además del aumento en los dominios amorfos en el polímero, donde se centra la biodegradación del material. Por otro lado, mediante las reacciones de cicloadición (clic), se logró la conjugación de biomoléculas como el colesterol, ácido linoleico y oleico con el copolímero obtenido. Estas biomoléculas fueron adecuadas con grupos alquino para permitir la reacción con los grupos pendientes azido del copolímero; cada biomolécula requirió de halogenación y amidación. Los productos obtenidos fueron caracterizados por FTIR y RMN-1H constatando la presencia de la biomolécula y el copolímero. Finalmente bajó la técnica de nanoprecipitación se sintetizaron partículas cargadas de curcumina (curcuminoides), encontrando que estas poseen un tamaño entre 160 y 450nm y una estabilidad electrostática en solución, además de una concentración entre 10-30% de curcumina. También, se enuncian los efectos de la interacción entre el copolímero, las biomoléculas y la curcumina, proponiendo un modelo esférico injertado para estas preparaciones, que mostraron actividad antibacteriana en microorganismos Gram negativos y positivos. (Texto tomado de la fuente)This research is based on the synthesis of polycaprolactone (PCL) and copolymers thereof, by means of ring-opening polymerization incorporating lipase-type enzymes as catalysts. In principle, the synthesis of PCL has been focused on the action of chemical catalysts and high experimental demands, which are opposed to environmental and human health, making it evident that alternatives that favor the synthesis of polyester and its copolymers, in addition to environmental care, are required. That is why it is recognized that the enzymatic ring-opening polymerization (eROP) using lipases together with "mild" reaction conditions, constitutes the synthesis of functionalized copolymers of PCL as an environmentally friendly process. To date, eROP addresses aspects such as the types of enzymes and their origin, as well as the effects of experimental conditions (solvent, temperature, initiators, etc.) on polymer properties and lipase stability; it is necessary to emphasize that these explorations are focused on linear and telechelic polymers, while more versatile and functional structures are in demand, this being a field less addressed by enzymatic polymerization. Initially, the enzymatic activity on eROP of caprolactone (ℇ -CL) from two lipases with different origin and disposition were compared, the first being Candida antarctica type B lipase (CALB) (N-435) and the second porcine pancreatic lipase (PPL). Both enzymes in eROP allowed the opening of the ℇ-CL ring, PPL evidenced a 26% conversion and the formation of acidic species and dimer and trimer type oligomers in more than 36 hours of reaction, while 100% conversion of the monomer was generated by N-435 in 4 hours of reaction, with a high molecular weight PCL (Mn: 14.1 kDa). In this sense, N-435 showed control of polymerization and better efficiency versus PPL, agreeing with the higher activity demonstrated in the hydrolysis of tri- and monoglycerides. Likewise, N-435 in SEM micrographs, exhibits that the enzyme support is mechanically affected and can influence the reusability of the catalyst. Subsequently, the "mild" reaction conditions that allowed the synthesis of PCL with N-435 and with high yields in its molecular weight and degrees of conversion, were established under comparison of variations in temperature, solvents and concentrations with the catalyst. It was stipulated that the reaction at 70ºC, in toluene and with a 10% concentration of N-435 with respect to the monomer, allow 100% conversion of ℇ-CL, good properties in PCL and lower energy requirements with respect to chemical catalysts. The effects that the variation of temperature, solvents and concentrations have on the reaction performance are also pointed out, finding among these, high polydispersion (Ð), decrease of molecular weights and conversions. With the compendium of the "mild" reaction conditions and the high activity of N-435, the copolymer α-azido-ε-caprolactone-co-caprolactone (Poly (α-N3-CL-co-CL)) was obtained at two different molecular weights (Mn: 14.7 and 9.5 kDa) and 100% conversion, demonstrating the control of N-435 on polymerization. This copolymer exhibited a different thermal behavior than pure PCL, since the presence of azide groups in the polymer chain decreases the melting temperatures and therefore the crystallization. Because of this effect, it is estimated that the crystals of the copolymer are smaller in size and different in shape, in addition to the increase in the amorphous domains in the polymer, where the biodegradation of the material is centered. On the other hand, by means of cycloaddition reactions (click), the conjugation of biomolecules such as cholesterol, linoleic and oleic acid with the obtained copolymer was achieved. These biomolecules were fit with alkyne groups to allow reaction with the outstanding azido groups of the copolymer; each biomolecule required halogenation and aminolysis. The obtained products were characterized by FTIR and 1H-NMR confirming the presence of the biomolecule and the copolymer. Finally, using the nanoprecipitation technique, curcumin charged particles (curcuminoids) were synthesized, finding that they have a size between 160 and 450 nm and an electrostatic stability in solution, in addition to a concentration between 10-30% of curcumin. Also, the effects of the interaction between the copolymer, biomolecules and curcumin are enunciated, proposing a spherical grafted model for these preparations, which showed antibacterial activity in Gram negative and positive microorganisms.MaestríaMagíster en Ciencias - QuímicaSíntesis de polímerosxix, 102 páginasapplication/pdfspaUniversidad Nacional de ColombiaBogotá - Ciencias - Maestría en Ciencias - QuímicaDepartamento de QuímicaFacultad de CienciasBogotá, ColombiaUniversidad Nacional de Colombia - Sede Bogotá540 - Química y ciencias afines::547 - Química orgánicaPOLIMERIZACION DE ABERTURA DE ANILLORing-opening polymerizationPolímerosLipasasPolicaprolactonaCurcuminaBiomoléculasCopolímeroeROPCurcuminBiomoleculesLipasesPolycaprolactoneCopolymerSíntesis de polímeros de caprolactona mediante polimerización por apertura de anillo enzimático implementando lipasas como proceso biocatalítico con enfoque en química verdeSynthesis of caprolactone polymers by enzymatic ring-opening polymerization implementing lipases as a biocatalytic process with a focus on green chemistryTrabajo de grado - Maestríainfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/acceptedVersionTexthttp://purl.org/redcol/resource_type/TMAjiboye, A. 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Process Biochemistry, 46(10), 1900–1908. https://doi.org/10.1016/j.procbio.2011.07.016EstudiantesInvestigadoresMaestrosORIGINAL1022982935.2022.pdf1022982935.2022.pdfTesis de Maestría en Ciencias - Químicaapplication/pdf4060935https://repositorio.unal.edu.co/bitstream/unal/81524/1/1022982935.2022.pdf97c1dae908d9cac5d1d59c7b6b4ee81eMD51LICENSElicense.txtlicense.txttext/plain; charset=utf-84074https://repositorio.unal.edu.co/bitstream/unal/81524/2/license.txt8153f7789df02f0a4c9e079953658ab2MD52THUMBNAIL1022982935.2022.pdf.jpg1022982935.2022.pdf.jpgGenerated Thumbnailimage/jpeg4863https://repositorio.unal.edu.co/bitstream/unal/81524/3/1022982935.2022.pdf.jpga84c73f2f58abc873e8e5c28c47f8cceMD53unal/81524oai:repositorio.unal.edu.co:unal/815242023-08-04 23:04:42.855Repositorio Institucional Universidad Nacional de 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