Diazo compounds for the bioreversible esterification of proteins
| Autor: | Kristen A. Andersen, Amy K. F. Davis, Ronald T. Raines, Jo E. Lomax, Nicholas A. McGrath |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Aqueous solution 010405 organic chemistry Carboxylic acid Chemical modification A protein General Chemistry Prodrug 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Hydrolysis chemistry.chemical_compound chemistry Organic chemistry Reactivity (chemistry) Diazo |
| Zdroj: | Chemical Science. 6:752-755 |
| ISSN: | 2041-6539 2041-6520 |
| DOI: | 10.1039/c4sc01768d |
| Popis: | A diazo compound is shown to convert carboxylic acids to esters efficiently in an aqueous environment. The basicity of the diazo compound is critical: low basicity does not lead to a reaction but high basicity leads to hydrolysis. This reactivity extends to carboxylic acid groups in a protein. The ensuing esters are hydrolyzed by human cellular esterases to regenerate protein carboxyl groups. This new mode of chemical modification could enable the key advantages of prodrugs to be translated from small-molecules to proteins. |
| Databáze: | OpenAIRE |
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