A new synthesis of the oligosaccharide domain of acarbose.
Synthesis of the oligosaccharide domain of acarbose was reinvestigated and was optimally performed using a maltosidic acceptor, already bearing a alpha-D-Glc-(1-->4)-D-Glc bond, and a new D-fucopyranosyl donor. The crucial glycosylation step was improved by varying three different parameters and notably by focusing on the C-4 protecting group of the fucosyl residue, solvent and promoter. The resulting trisaccharide was further transformed into an electrophilic species in order to open further derivatization perspectives for designing new acarbose analogues. Substitution reactions were efficiently carried out with azide and thiocyanate anions. Two other potentially interesting trisaccharidic compounds were also synthesized, i.e. the C-4III amine and the corresponding isothiocyanate.
Périon
Régis
R
Synthèses et Activations de Biomolécules, UMR CNRS 6052, Ecole Nationale Supérieure de Chimie de Rennes, Avenue du Général Leclerc, F-35700 Rennes, France.
Lemée
Lénaïck
L
Ferrières
Vincent
V
Duval
Raphaël
R
Plusquellec
Daniel
D
D020909:Acarbose / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D005643:Fucose / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D006031:Glycosylation; D007004:Hypoglycemic Agents / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D007004:Hypoglycemic Agents; D013865:Thioglycosides; D014312:Trisaccharides; D005643:Fucose; D008320:Maltose; D020909:Acarbose; D005690:Galactose