Fluorogenic peptide substrates for assay of aspartyl proteinases

Anal Biochem. 1996 Feb 15;234(2):113-8. doi: 10.1006/abio.1996.0062.

Abstract

Via a combination of chemical and enzymatic synthesis, new hexapeptide substrates convenient for use in activity assessment of several aspartyl proteinases--porcine pepsin, human pepsin, gastricsin, and cathepsin D--were prepared. These peptide derivatives, o-aminobenzoyl-Ala-Ala-Phe-Phe-Ala-Ala-p-nitroanilide and N-(o-aminobenzoyl-Ala-Ala-Phe-Phe-Ala-Ala)-N'-2,4-dinitrophenyl ethylenediamine, contain a fluorescent o-aminobenzoyl moiety as well as p-nitroaniline or N-2,4-dinitrophenyl ethylenediamine--the groups that cause fluorescence quenching. Aspartyl proteinases hydrolyze the Phe-Phe peptide bond in the substrates, which diminishes quenching due to separation of the fluorescent and quenching moieties and leads to an increase in the fluorescence intensity of o-aminobenzoyl residue. Abz-Ala-Ala-Phe-Phe-Ala-Ala-Ded, being fairly well hydrolyzed by HIV proteinase, might be used for assay of this enzyme.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Aminobenzoates / chemistry*
  • Animals
  • Cathepsin D / analysis*
  • Fluorometry
  • Humans
  • Molecular Sequence Data
  • Molecular Structure
  • Oligopeptides / chemistry*
  • Pepsin A / analysis*
  • Swine

Substances

  • 2-aminobenzoyl-alanyl-alanyl-phenylalanyl-phenylalanyl-alanyl-alanyl-4-nitroanilide
  • Aminobenzoates
  • N-(2-aminobenzoyl-alanyl-alanyl-phenylalanyl-phenylalanyl-alanyl-alanyl)-N'-2,4-dinitrophenylethylenediamine
  • Oligopeptides
  • Pepsin A
  • gastricsin
  • Cathepsin D