A method for esterification of one or more carboxylic acid groups in a compound containing one or more carboxylic acid groups wherein the esterification reagent is a diazo-compound of formula:
wherein the R1 and R2 groups of the diazo compound are selected such that the corresponding organic compound of formula:
exhibits a —C—H pKa value between 18 and 29 as measured in DMSO. Specific reagents and methods for esterification are provided. The esterification reagents provided exhibit high selectivity for esterification of carboxylic acid groups over reaction with amine, alcohol or thiol groups in the compound containing one or more carboxylic acid groups. The method can be used to selectively esterify carboxylic acid groups in peptides or proteins.
A method for esterification of one or more carboxylic acid groups in a compound containing one or more carboxylic acid groups wherein the esterification reagent is a diazo-compound of formula:
wherein the R
1
and R
2
groups of the diazo compound are selected such that the corresponding organic compound of formula:
exhibits a —C—H pKa value between 18 and 29 as measured in DMSO. Specific reagents and methods for esterification are provided. The esterification reagents provided exhibit high selectivity for esterification of carboxylic acid groups over reaction with amine, alcohol or thiol groups in the compound containing one or more carboxylic acid groups. The method can be used to selectively esterify carboxylic acid groups in peptides or proteins.
Diazo compounds for the bioreversible esterification of proteins
作者:Nicholas A. McGrath、Kristen A. Andersen、Amy K. F. Davis、Jo E. Lomax、Ronald T. Raines
DOI:10.1039/c4sc01768d
日期:——
A diazo compound is shown to convert carboxylic acids to esters efficiently in an aqueous environment.