Optimized Diazo Scaffold for Protein Esterification

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...

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Veröffentlicht in:	Organic letters 2015-05, Vol.17 (10), p.2358-2361
Hauptverfasser:	Mix, Kalie A, Raines, Ronald T
Format:	Artikel
Sprache:	eng
Schlagworte:	Azo Compounds - chemistry Carboxylic Acids - chemistry Esters - chemical synthesis Esters - chemistry Models, Molecular Molecular Structure Proteins - chemical synthesis Proteins - chemistry
Online-Zugang:	Volltext
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Beschreibung
Zusammenfassung:	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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/acs.orglett.5b00840