title: Furan-based acetylating agent for the chemical modification of proteins.
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.
authors.affiliation: Laboratory of Catalysis, Department of Chemistry, University of Delhi, North Campus, Delhi 110007, India.
authors.forename: Sudipta
authors.initials: S
authors.lastname: De
authors.affiliation: Dr. B.R. Ambedkar Centre for Biomedical Research, University of Delhi, North Campus, Delhi 110007, India.
authors.forename: Tarun
authors.initials: T
authors.lastname: Kumar
authors.affiliation: Laboratory of Catalysis, Department of Chemistry, University of Delhi, North Campus, Delhi 110007, India.
authors.forename: Ashish
authors.initials: A
authors.lastname: Bohre
authors.affiliation: Dr. B.R. Ambedkar Centre for Biomedical Research, University of Delhi, North Campus, Delhi 110007, India.
authors.forename: Laishram R
authors.initials: LR
authors.lastname: Singh
authors.affiliation: Laboratory of Catalysis, Department of Chemistry, University of Delhi, North Campus, Delhi 110007, India. Electronic address: bsaha@chemistry.du.ac.in.
authors.forename: Basudeb
authors.initials: B
authors.lastname: Saha
mesh_terms: D000107:Acetylation; D000818:Animals; D002417:Cattle; D045304:Cytochromes c / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D008239:Lysine / Q000737:chemistry*; D008958:Models, Molecular; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D005663:Furans; D007202:Indicators and Reagents; D045304:Cytochromes c; D008239:Lysine; C039281:furan
keywords: Cytochrome c; Furan-based acetylating agent; Lysine residues; N-acetylation; Protein modification