title: Chemical modification of guanidinium groups of vasoactive intestinal peptide.
abstract: Molecular characterization of receptors depends on the availability of ligand derivatives carrying a reactive group to covalently link the active sites. Two vasoactive intestinal peptide (VIP) derivatives, each labeled either at the two arginine residues 12 and 14 or singly in position 14, were prepared. In the first case, this was achieved by a selective chemical modification using azidophenylglyoxal. In the second, the amino acids of VIP, buried in the active site of the receptor, were protected and one arginine residue of bound VIP was successfully modified using azidophenylglyoxal. The two molecules were resolved by radioimmunocompetition and reversed phase high performance liquid chromatography. Identification of sites of labeling was achieved by tryptic peptide mapping and amino acid analysis. One derivative (Az-Bz-Arg14-VIP) retains a high binding affinity for the receptor and was found to be biologically active. The present method yields a derivative which is useful in structural analysis of the receptor.
mesh_terms: D000447:Aldehydes; D000596:Amino Acids / Q000032:analysis; D000818:Animals; D001120:Arginine; D001386:Azides; D001667:Binding, Competitive; D003432:Cross-Linking Reagents; D000242:Cyclic AMP / Q000096:biosynthesis; D019791:Guanidine; D006146:Guanidines; D066298:In Vitro Techniques; D010658:Phenylglyoxal / Q000031:analogs & derivatives; D010777:Photochemistry; D051381:Rats; D011964:Receptors, Gastrointestinal Hormone / Q000378:metabolism; D018005:Receptors, Vasoactive Intestinal Peptide; D014660:Vasoactive Intestinal Peptide / Q000378:metabolism / Q000494:pharmacology
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D001386:Azides; D003432:Cross-Linking Reagents; D006146:Guanidines; D011964:Receptors, Gastrointestinal Hormone; D018005:Receptors, Vasoactive Intestinal Peptide; D014660:Vasoactive Intestinal Peptide; C032404:4-azidophenylglyoxal; D001120:Arginine; D000242:Cyclic AMP; D019791:Guanidine; D010658:Phenylglyoxal