title: Synthesis of a bicyclic analog of L-iduronic acid adopting the biologically relevant 2S0 conformation.
abstract: The synthesis of a bicyclic analogue of the naturally occurring alpha-L-iduronic acid locked in a biologically active (2)S0 skewboat conformation is disclosed. The desired (2)S0 conformation has been obtained by tethering the C-2 and C-5 carbon atoms of the sugar ring with a dimethyloxy bridge and confirmed by NMR and molecular modeling. The new mimic displays the exact hydroxyl pattern of alpha-L-iduronic acid, a major monosaccharide component of glycosaminoglycans and thus represents a closer mimic of the latter, compared to previously reported bicyclic analogs.
authors.affiliation: Ecole Normale Supérieure, Département de Chimie, UMR 8642 Associée au CNRS, 24 rue Lhomond, 75231 Paris Cedex 05, France.
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Herrera
authors.forename: Marita T
authors.initials: MT
authors.lastname: Beneitez
authors.forename: Luis
authors.initials: L
authors.lastname: Amorim
authors.forename: F Javier
authors.initials: FJ
authors.lastname: Cañada
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
authors.forename: Pierre
authors.initials: P
authors.lastname: Sinaÿ
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002236:Carbohydrate Conformation; D006025:Glycosaminoglycans / Q000737:chemistry; D006493:Heparin / Q000737:chemistry; D007067:Iduronic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001643:Bridged Bicyclo Compounds; D006025:Glycosaminoglycans; D007202:Indicators and Reagents; D009844:Oligosaccharides; D007067:Iduronic Acid; D006493:Heparin