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Org Lett. 2015 May 15;17(10):2358-61. doi: 10.1021/acs.orglett.5b00840. Epub 2015 May 4.

Optimized diazo scaffold for protein esterification.

Author information

1
†Department of Biochemistry and ‡Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.

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.

PMID:
25938936
PMCID:
PMC4670563
DOI:
10.1021/acs.orglett.5b00840
[Indexed for MEDLINE]
Free PMC Article

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