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2007:
Herrera Antonio J; Beneitez Marita T; Amorim Luis; Cañada F Javier; Jiménez-Barbero Jesús; Sinaÿ Pierre; Blériot Yves
Synthesis of a bicyclic analog of L-iduronic acid adopting the biologically relevant 2S0 conformation.
Carbohydrate research 2007;
342(
12-13):.
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.
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