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 rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent.
†Department of Biochemistry and ‡Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
Kalie A
KA
Mix
†Department of Biochemistry and ‡Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
Ronald T
RT
Raines
D001391:Azo Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry
D001391:Azo Compounds; D002264:Carboxylic Acids; D004952:Esters; D011506:Proteins