title: Parallel synthesis of peptide-like macrocycles containing imidazole-4,5-dicarboxylic acid.
abstract: We prepared a series of peptide-like 14-membered macrocycles containing an imidazole-4,5-dicarboxylic acid scaffold by using known coupling reagents and protecting group strategies. Yields of the purified macrocycles were poor on average, yet seemingly independent of amino acid substitution or stereochemistry. The macrocycles retain some level of conformational variability as observed by both molecular modeling and X-ray crystallography. These macrocycles represent a new class of structures for further development and for future application in high-throughput screening against a variety of biological targets.
authors.affiliation: Department of Pharmacology and Toxicology, The University of Arizona, Tucson, AZ 85724, USA.
authors.forename: Zhigang
authors.initials: Z
authors.lastname: Xu
authors.forename: Kraig A
authors.initials: KA
authors.lastname: Wheeler
authors.forename: Paul W
authors.initials: PW
authors.lastname: Baures
mesh_terms: D019943:Amino Acid Substitution; D000596:Amino Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003998:Dicarboxylic Acids / Q000138:chemical synthesis*; D055808:Drug Discovery; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D057786:Peptidomimetics / Q000138:chemical synthesis*
chemical_list: D000596:Amino Acids; D003998:Dicarboxylic Acids; D007093:Imidazoles; D057786:Peptidomimetics