Synthesis of a bicyclic analog of L-iduronic acid adopting the biologically relevant 2S0 conformation.
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.
Herrera
Antonio J
AJ
Ecole Normale Supérieure, Département de Chimie, UMR 8642 Associée au CNRS, 24 rue Lhomond, 75231 Paris Cedex 05, France.
Beneitez
Marita T
MT
Amorim
Luis
L
Cañada
F Javier
FJ
Jiménez-Barbero
Jesús
J
Sinaÿ
Pierre
P
Blériot
Yves
Y
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*
D001643:Bridged Bicyclo Compounds; D006025:Glycosaminoglycans; D007202:Indicators and Reagents; D009844:Oligosaccharides; D007067:Iduronic Acid; D006493:Heparin