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Título: | pKa Modulation of Pyrrolidine-Based Catalytic Polymers Used for the Preparation of Glycosyl Hydrazides at Physiological pH and Temperature |
Autor: | Vargas, E. L.; Velázquez, J. A.; Rodrigo, Eduardo; Reinecke, Helmut CSIC ORCID; Rodríguez-Hernández, Juan CSIC ORCID; Fernández-Mayoralas, Alfonso CSIC ORCID ; Gallardo Ruiz, Alberto CSIC ORCID; Cid, M. Belén | Palabras clave: | Enzyme-like organocatalysis Iminium activation Pyrrolidine pKa modulation Polymers Hydrazones |
Fecha de publicación: | 2020 | Editor: | ACS Publications | Citación: | ACS Applied Biomaterials 3: 1955-1967 (2020) | Resumen: | Inspired by the ability of enzymes to use the surrounding hydrophobic and/or polarizable groups to modulate the pK of a given amino acid, we designed a series of soluble polymers able to decrease the basicity of pyrrolidine (from 11.2 to 8.6 pK units), which clearly increases its aminocatalytic activity at physiological pH in C═N bond formation reactions via ion iminium activation. Other parameters such as charge density, hydrophobic/hydrophilic balance, and aggregation state have been studied as important factors in the catalytic activity of the polymers for a given substrate. To demonstrate the utility of our approach, an optimal pyrrolidine-based catalytic polymer has been used for the formation of C-N bonds between hydrazides and free sugars as the model system for the preparation of glycoconjugates. | Versión del editor: | http://dx.doi.org/10.1021/acsabm.9b01123 | URI: | http://hdl.handle.net/10261/217563 | DOI: | 10.1021/acsabm.9b01123 | Identificadores: | doi: 10.1021/acsabm.9b01123 issn: 2576-6422 |
Aparece en las colecciones: | (IQOG) Artículos (ICTP) Artículos |
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ACS App Bio Mater_2020.pdf | 1,04 MB | Adobe PDF | Visualizar/Abrir |
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