title: Synthesis of a family of cyclic peptide-based anion receptors.
abstract: We report here the design and synthesis of a family of novel backbone modified cyclic peptides, bearing dipicolylamine side chains for metal complexation and subsequent anion binding studies. Two approaches to the cyclic peptides were investigated. Initially, a stepwise approach was employed, involving solid-phase assembly of oxazole-based building blocks, followed by solution-phase macrolactamisation of the resulting linear precursor. The alternative strategy involved the formation of linear bisoxazole fragments in solution-phase, followed by a cyclodimerisation reaction. The zinc(II) complexes of these receptors bind selectively to di- and tri-phosphate ions over hydrogenphosphate.
authors: School of Chemistry, The University of Sydney, 2006, NSW, Australia.
authors: Stephen J
authors: SJ
authors: Butler
authors: Katrina A
authors: KA
authors: Jolliffe
mesh_terms: D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis; D000838:Anions / Q000737:chemistry; D003500:Cyclization; D019281:Dimerization; D047029:Lactams, Macrocyclic / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D010848:Picolinic Acids / Q000737:chemistry
chemical_list: C501847:2,2'-dipicolylamine; D000588:Amines; D000596:Amino Acids; D000838:Anions; D047029:Lactams, Macrocyclic; D010080:Oxazoles; D010456:Peptides, Cyclic; D010848:Picolinic Acids