Synthetic and structural studies of α-sialyl-(2 -> 6) and α-sialyl-(2 -> 3) 1-deoxynojirimycin derivatives potentially used for biomedical applications

Article abstract of DOI:10.1016/0008-6215(95)00068-5

Suitably protected derivatives of 1-deoxynojirimycin (1,5-dideoxy-1,5-imino-D-glucitol, DNJ) and its D-galacto analog were coupled with 2-thioglycosides of N-acetylneuraminic acid.The resulying disaccharides were converted into a variety of α-sialyl-(2 -> 6)- and α-sialyl-(2 -> 3)-DNJ derivatives, including the cyclic lactams 6-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',5-lactam)-1,5-dideoxy-1,5-imino-D-glucitol and -D-galactitol.The structural features of the synthetic compounds were investigated by ion-spray mass and 1H NMR spectrometry.The ¹C₄ conformation of N-tert-butoxycarbonyl-DNJ, a synthetic intermediate having the gluco configuration, was confirmed by X-ray crystallography.Keywords: Synthetic and structural studies; α-Sialyl-(2 -> 6); α-Sialyl-(2 -> 3); Deoxynojirimycin derivatives; Biomedical applications.