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Optimized diazo scaffold for protein esterification.


ABSTRACT: The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent.

SUBMITTER: Mix KA 

PROVIDER: S-EPMC4670563 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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Optimized diazo scaffold for protein esterification.

Mix Kalie A KA   Raines Ronald T RT  

Organic letters 20150504 10


The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent. ...[more]

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