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Title

P Ka Modulation of Pyrrolidine-Based Catalytic Polymers Used for the Preparation of Glycosyl Hydrazides at Physiological pH and Temperature

AuthorsVargas, E. L.; Velázquez, J. A.; Rodrigo, Eduardo; Reinecke, Helmut ; Rodríguez-Hernández, Juan ; Fernández-Mayoralas, Alfonso ; Gallardo, Alberto ; Cid, M. Belén
KeywordsEnzyme-like organocatalysis
Iminium activation
Pyrrolidine
pKa modulation
Polymers
Hydrazones
Issue Date2020
PublisherACS Publications
CitationACS Applied Biomaterials 3: 1955-1967 (2020)
AbstractInspired 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.
Publisher version (URL)http://dx.doi.org/10.1021/acsabm.9b01123
URIhttp://hdl.handle.net/10261/217563
Identifiersdoi: 10.1021/acsabm.9b01123
issn: 2576-6422
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