Effect of methylation on the side-chain pKa value of arginine

Protein Sci. 2016 Feb;25(2):479-86. doi: 10.1002/pro.2838. Epub 2015 Nov 25.

Abstract

Arginine methylation is important in biological systems. Recent studies link the deregulation of protein arginine methyltransferases with certain cancers. To assess the impact of methylation on interaction with other biomolecules, the pKa values of methylated arginine variants were determined using NMR data. The pKa values of monomethylated, symmetrically dimethylated, and asymmetrically dimethylated arginine are similar to the unmodified arginine (14.2 ± 0.4). Although the pKa value has not been significantly affected by methylation, consequences of methylation include changes in charge distribution and steric effects, suggesting alternative mechanisms for recognition.

Keywords: NMR spectroscopy; arginine; methylation; methyltransferase; pH titration; pKa determination.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arginine / analogs & derivatives*
  • Arginine / chemistry
  • Hydrogen-Ion Concentration
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Models, Molecular
  • Osmolar Concentration

Substances

  • Arginine