Furan-based acetylating agent for the chemical modification of proteins

Bioorg Med Chem. 2015 Feb 15;23(4):791-6. doi: 10.1016/j.bmc.2014.12.053. Epub 2014 Dec 30.

Abstract

We have synthesized a furan-based acetylating agent, 2,5-bisacetoxymethylfuran (BAMF) from carbohydrate derived 5-hydroxymethylfurfural (HMF) and studied its acetylation activity with amines and cytochrome c. The results show that BAMF can modify proteins in biological conditions without affecting their structure and function. The modification of cytochrome c with BAMF occurred through the reduction of heme center, but there was no change in the coordination property of iron and the tertiary structure of cytochrome c. Further analysis using MALDI-TOF-MS spectrometer suggests that BAMF selectively targeted lysine amino acid of cytochrome c under our experimental conditions. Kinetics study revealed that the modification of cytochrome c with BAMF took place at faster rates than aspirin.

Keywords: Cytochrome c; Furan-based acetylating agent; Lysine residues; N-acetylation; Protein modification.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Animals
  • Cattle
  • Cytochromes c / chemistry*
  • Furans / chemistry*
  • Indicators and Reagents / chemistry
  • Lysine / chemistry*
  • Models, Molecular
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Furans
  • Indicators and Reagents
  • Cytochromes c
  • Lysine
  • furan