Diazo compounds for the bioreversible esterification of proteins

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 e...

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Bibliographic Details
Published in:	Chemical science (Cambridge) Vol. 6; no. 1; pp. 752 - 755
Main Authors:	McGrath, Nicholas A, Andersen, Kristen A, Davis, Amy K F, Lomax, Jo E, Raines, Ronald T
Format:	Journal Article
Language:	English
Published:	England 01-01-2015
Subjects:	Aqueous environments Basicity Carboxyl group Carboxylic acids Chemical compounds Esters Proteins
Online Access:	Get full text
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	2041-6520 2041-6539
DOI:	10.1039/c4sc01768d