Diazotrifluoropropionamido-containing prenylcysteines: syntheses and applications for studying isoprenoid-protein interactions.
Photoaffinity-labeled prenylcysteines (1 and 2) incorporating a diazotrifluoropropionamide-based photophore have been prepared. Photolyses of 2 in the presence of RhoGDI, a protein that interacts with prenylated proteins, and prenylcysteine-containing competitors demonstrate the effectiveness of this photoaffinity-labeled analogue as a tool for studying isoprenoid binding sites.
Kale
Tamara A
TA
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Distefano
Mark D
MD
D000577:Amides / Q000737:chemistry*; D001345:Autoradiography; D001577:Benzophenones / Q000737:chemistry; D001665:Binding Sites; D001667:Binding, Competitive; D001710:Biotin / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D003979:Diazonium Compounds / Q000737:chemistry*; D020730:Guanine Nucleotide Dissociation Inhibitors / Q000737:chemistry* / Q000378:metabolism; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000737:chemistry; D010782:Photolysis; D017368:Protein Prenylation; D019809:Streptavidin / Q000737:chemistry; D062947:rho-Specific Guanine Nucleotide Dissociation Inhibitors
D000577:Amides; D001577:Benzophenones; D003432:Cross-Linking Reagents; D003979:Diazonium Compounds; D020730:Guanine Nucleotide Dissociation Inhibitors; D019920:Photoaffinity Labels; C474589:diazotrifluoropropionamide; D062947:rho-Specific Guanine Nucleotide Dissociation Inhibitors; D001710:Biotin; C047723:benzophenone; D019809:Streptavidin; D003545:Cysteine