title: Metathesis of structurally preorganized bivalent carbohydrates. Synthesis of macrocyclic and oligomeric scaffolds.
abstract: [reaction: see text] Bivalent carbohydrate substrates for metathesis were synthesized from glucuronic acid and phenylene-1,4-diamine. The substrate secondary structure depends on whether secondary or tertiary amides are present, and this influences the course of the metathesis reaction leading to novel multivalent scaffolding. Molecular modeling suggests that a very rigid macrocyclic scaffold has potential for the development of alpha-helix peptidomimetics.
authors.affiliation: Centre for Synthesis and Chemical Biology, Chemistry Department, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
authors.forename: Trinidad
authors.initials: T
authors.lastname: Velasco-Torrijos
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D003959:Diamines / Q000737:chemistry; D020723:Glucuronic Acid / Q000737:chemistry; D008024:Ligands; D018716:Molecular Mimicry; D009842:Oligopeptides / Q000138:chemical synthesis; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D017433:Protein Structure, Secondary; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D003959:Diamines; D008024:Ligands; D009842:Oligopeptides; D010456:Peptides, Cyclic; D020723:Glucuronic Acid