Issue 1, 2015

Diazo compounds for the bioreversible esterification of proteins

Abstract

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.

Graphical abstract: Diazo compounds for the bioreversible esterification of proteins

Supplementary files

Article information

Article type
Edge Article
Submitted
14 Jun 2014
Accepted
27 Sep 2014
First published
01 Oct 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 752-755

Author version available

Diazo compounds for the bioreversible esterification of proteins

N. A. McGrath, K. A. Andersen, A. K. F. Davis, J. E. Lomax and R. T. Raines, Chem. Sci., 2015, 6, 752 DOI: 10.1039/C4SC01768D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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