Optimized diazo scaffold for protein esterification

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


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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Azo Compounds / chemistry*
  • Carboxylic Acids / chemistry
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Models, Molecular
  • Molecular Structure
  • Proteins / chemical synthesis*
  • Proteins / chemistry


  • Azo Compounds
  • Carboxylic Acids
  • Esters
  • Proteins