Aqueous Solutions of Peptides and Trialkylamines Lead to Unexpected Peptide Modification

Molecules. 2021 Oct 27;26(21):6481. doi: 10.3390/molecules26216481.

Abstract

When trialkylamines are added to buffered solutions of peptides, unexpected adducts can be formed. These adducts correspond to Schiff base products. The source of the reaction is the unexpected presence of aldehydes in amines. The aldehydes can be detected in a few ways. Most importantly, they can lead to unanticipated results in proteomics experiments. Their undesirable effects can be minimized through the addition of other amines.

Keywords: Schiff base; protein modification; triethylamine.

MeSH terms

  • Aldehydes
  • Amines / chemistry*
  • Amino Acid Sequence
  • Hemoglobins / chemistry
  • Peptides / chemistry*
  • Polyamines / chemistry
  • Proteins / chemistry
  • Proteolysis
  • Schiff Bases
  • Solutions
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Aldehydes
  • Amines
  • Hemoglobins
  • Peptides
  • Polyamines
  • Proteins
  • Schiff Bases
  • Solutions