title: Enzymatic incorporation of orthogonally reactive prenylazide groups into peptides using geranylazide diphosphate via protein farnesyltransferase: implications for selective protein labeling.
abstract: Protein farnesyltransferase (PFTase) catalyzes the attachment of a geranyl azide moiety to a peptide substrate, N-dansyl-Gly-Cys-Val-Ile-Ala-OH. The resulting azide-containing peptide was derivatized with a triphenylphosphine-based reagent to generate an O-alkyl imidate-linked product, rather than the amide-linked material expected via a Staudinger reaction. Since the CAAX box recognition motif (where the internal A residues are aliphatic amino acids) modified by PFTase can be incorporated into the C-terminus of virtually any polypeptide, this two-step procedure provides a general method for incorporating a diverse range of chemical modifications specifically near the C-terminus of proteins.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
authors.forename: Matthew W
authors.initials: MW
authors.lastname: Rose
authors.forename: Juhua
authors.initials: J
authors.lastname: Xu
authors.forename: Tamara A
authors.initials: TA
authors.lastname: Kale
authors.forename: George
authors.initials: G
authors.lastname: O'Doherty
authors.forename: George
authors.initials: G
authors.lastname: Barany
authors.forename: Mark D
authors.initials: MD
authors.lastname: Distefano
mesh_terms: D019883:Alkyl and Aryl Transferases / Q000378:metabolism*; D001386:Azides / Q000737:chemistry; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D011106:Polyisoprenyl Phosphates / Q000737:chemistry; D017368:Protein Prenylation; D011506:Proteins / Q000737:chemistry / Q000378:metabolism*
chemical_list: D001386:Azides; D007202:Indicators and Reagents; D011106:Polyisoprenyl Phosphates; D011506:Proteins; D019883:Alkyl and Aryl Transferases; C064911:p21(ras) farnesyl-protein transferase