Person: García Oliva, Cecilia María
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First Name
Cecilia María
Last Name
García Oliva
Affiliation
Universidad Complutense de Madrid
Faculty / Institute
Farmacia
Department
Química en Ciencias Farmacéuticas
Area
Identifiers
6 results
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Now showing 1 - 6 of 6
Item Enzymatic Synthesis and Molecular Modelling Studies of Rhamnose Esters Using Lipase from Pseudomonas stutzeri(International Journal of Molecular Sciences, 2022) García Oliva, Cecilia María; Perona Requena, Almudena; Rumbero, Ángel; Hoyos Vidal, María Pilar; Hernáiz Gómez-Degano, María Josefa; Hernáiz Gómez-Degano, María JosefaRhamnolipids are becoming an important class of glycolipid biosurfactants. Herein, we describe for the first time the enzymatic synthesis of rhamnose fatty acid esters by the transesterification of rhamnose with fatty acid vinyl esters, using lipase from Pseudomonas stutzeri as a biocatalyst. The use of this lipase allows excellent catalytic activity in the synthesis of 4-O-acylrhamnose (99% conversion and full regioselectivity) after 3 h of reaction using tetrahydrofuran (THF) as the reaction media and an excess of vinyl laurate as the acyl donor. The role of reaction conditions, such as temperature, the substrates molar ratio, organic reaction medium and acyl donor chain-length, was studied. Optimum conditions were found using 35 °C, a molar ratio of 1:3 (rhamnose:acyldonor), solvents with a low logP value, and fatty acids with chain lengths from C4 to C18 as acyl donors. In hydrophilic solvents such as THF and acetone, conversions of up to 99–92% were achieved after 3 h of reaction. In a more sustainable solvent such as 2-methyl-THF (2-MeTHF), high conversions were also obtained (86%). Short and medium chain acyl donors (C4–C10) allowed maximum conversions after 3 h, and long chain acyl donors (C12–C18) required longer reactions (5 h) to get 99% conversions. Furthermore, scaled up reactions are feasible without losing catalytic action and regioselectivity. In order to explain enzyme regioselectivity and its ability to accommodate ester chains of different lengths, homology modelling, docking studies and molecular dynamic simulations were performed to explain the behaviour observed.- Project number: 337
Item Aula virtual para el aprendizaje práctico de la resolución enzimática de ácidos 2-arilpropiónicos usando estudios computacionales (Docking), hidrólisis enzimática y resonancia magnética nuclear (RMN)(2022) Perona Requena, Almudena; Hoyos Vidal, María Pilar; Ramírez López, Pedro; Aguilar-Amat, Aida Flores; Martínez Espinosa, Carlos Antonio; García Oliva, Cecilia María; Merchán del Real, Alejandro; Hadri, Nada; Jiménez Sánchez, Ana; Iniesta Meco, JuanAula virtual para el alumnado de Química Farmacéutica II y Biotecnología Farmacéutica II, en la cual, mediante elementos multimedia, aprenderán de forma autónoma a realizar la práctica de la resolución enzimática de ácidos 2-arilpropiónicos. En el aula virtual podrán aprender el uso de técnicas computacionales como el docking, así como a realizar reacciones enzimáticas y a interpretar el resultado de la reacción mediante resonancia magnética nuclear. Se usarán recursos educativos abiertos y enseñanza virtual. Item Acceptor Specificity of β-N-Acetylhexosaminidase from Talaromyces flavus: A Rational Explanation(International Journal of Molecular Sciences, 2019) García Oliva, Cecilia María; Hoyos Vidal, María Pilar; Petrásková, Lucie; Kulik, Natalia; Pelantová, Helena; Cabanillas, Alfredo H.; Rumbero, Ángel; Křen, Vladimír; Hernáiz Gómez-Degano, María Josefa; Bojarová, PavlaFungal β-N-acetylhexosaminidases, though hydrolytic enzymes in vivo, are useful tools in the preparation of oligosaccharides of biological interest. The β-N-acetylhexosaminidase from Talaromyces flavus is remarkable in terms of its synthetic potential, broad substrate specificity, and tolerance to substrate modifications. It can be heterologously produced in Pichia pastoris in a high yield. The mutation of the Tyr470 residue to histidine greatly enhances its transglycosylation capability. The aim of this work was to identify the structural requirements of this model β-N-acetylhexosaminidase for its transglycosylation acceptors and formulate a structure–activity relationship study. Enzymatic reactions were performed using an activated glycosyl donor, 4-nitrophenyl N-acetyl-β-d-glucosaminide or 4-nitrophenyl N-acetyl-β-d-galactosaminide, and a panel of glycosyl acceptors of varying structural features (N-acetylglucosamine, glucose, N-acetylgalactosamine, galactose, N-acetylmuramic acid, and glucuronic acid). The transglycosylation products were isolated and structurally characterized. The C-2 N-acetamido group in the acceptor molecule was found to be essential for recognition by the enzyme. The presence of the C-2 hydroxyl moiety strongly hindered the normal course of transglycosylation, yielding unique non-reducing disaccharides in a low yield. Moreover, whereas the gluco-configuration at C-4 steered the glycosylation into the β(1-4) position, the galacto-acceptor afforded a β(1-6) glycosidic linkage. The Y470H mutant enzyme was tested with acceptors based on β-glycosides of uronic acid and N-acetylmuramic acid. With the latter acceptor, we were able to isolate and characterize one glycosylation product in a low yield. To our knowledge, this is the first example of enzymatic glycosylation of an N-acetylmuramic acid derivative. In order to explain these findings and predict enzyme behavior, a modeling study was accomplished that correlated with the acquired experimental data.Item Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists(Chemistry - A European Journal, 2020) Cabanillas, Alfredo H; Rumbero, Ángel; García Oliva, Cecilia María; Perona Requena, Almudena; Hernáiz Gómez-Degano, María Josefa; Hoyos Vidal, María PilarCarbohydrates are involved in many important pathological processes, such as bacterial and viral infections, by means of carbohydrate-protein interactions. Glycoconjugates with multiple carbohydrates are involved in multivalent interactions, thus increasing their binding strengths to proteins. In this work, we report the efficient synthesis of novel muramic and glucuronic acid glycodendrimers as potential Dengue virus antagonists. Aromatic scaffolds functionalized with a terminal ethynyl groups were coupled to muramic and glucuronic acid azides by click chemistry through optimized synthetic strategies to afford the desired glycodendrimers with high yields. Surface Plasmon Resonance studies have demonstrated that the compounds reported bind efficiently to the Dengue virus envelope protein. Molecular modelling studies were carried out to simulate and explain the binding observed. These studies confirm that efficient chemical synthesis of glycodendrimers can be brought about easily offering a versatile strategy to find new active compounds against Dengue virus.- Project number: 208
Item Desarrollo y elaboración de recursos didácticos on line para fomentar el autoaprendizaje interactivo y la autoevaluación en Química Farmacéutica con el apoyo del Campus Virtual(2018) Hoyos Vidal, María Pilar; Hernáiz Gómez-Degano, María Josefa; Izquierdo Jiménez, Inmaculada; Alemán Sierra, Esther; García Oliva, Cecilia MaríaEn este Proyecto de Innovación Docente se ha pretendido de manera general optimizar las alternativas ofrecidas en el Campus Virtual, mediante el diseño, elaboración y evaluación de actividades didáticas on-line que permitan que el Aula Virtual se convierta en un apoyo activo en el proceso enseñanza-aprendizaje en la asignatura de Química Farmacéutica II. Se ha llevado a cabo la elaboración de cuestionarios interactivos de autoevaluación que permitan al alumno conocer la adecuación de los conocimientos adquiridos, y al docente poder realizar un seguimiento rápido de cada alumno. - Project number: 255
Item Herramientas de Aprendizaje para el Diseño 3D de Estructuras y Procesos Químicos mediante Programas Informáticos Gratuitos/Libres(2019) Hernáiz Gómez-Degano, María Josefa; Cabañas Criado, María Victoria; Peña López, Juan; Sánchez Salcedo, Sandra; Hoyos Vidal, María Pilar; García Fontecha, Ana; Baeza García, Alejandro; Moreno Pérez, José Manuel; García Oliva, Cecilia María; Piñero Barrera, Ignacio; Civera Tejuca, María Concepción; Perona Requena, AlmudenaEl objetivo propuesto en este proyecto de innovación docente fue el diseño, elaboración y evaluación de videos tutoriales on-line sobre el manejo de programas informáticos libres/gratuitos para el dibujo de moléculas químicas de interés farmacéutico, nomenclatura, cálculo de fórmulas y el diseño espacial de estructuras tridimensionales, que permitan que el alumno del Grado en Farmacia aprenda el manejo de programas siendo este un apoyo para la realización de su TFG y la defensa de mismo (Póster). Por otro lado, también se planteó el facilitar y animar a que los alumnos de cuarto y quinto curso del Grado en Farmacia presenten comunicaciones en el Congreso de Investigación para Estudiantes Pregraduados de Ciencias de la Salud celebrado todos los años en la UCM.