Synthetic and structural studies of alpha-sialyl-(2-->6) and alpha-sialyl-(2-->3) 1-deoxynojirimycin derivatives potentially useful for biomedical applications.
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 resulting disaccharides were converted into a variety of alpha-sialyl-(2-->6)-and alpha-sialyl-(2-->3)-DNJ derivatives, including the cyclic lactams 6-O-(5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyrano sylono- 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.
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D018360:Crystallography, X-Ray; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012794:Sialic Acids / Q000737:chemistry*
D006001:Glycoconjugates; D012794:Sialic Acids; D017485:1-Deoxynojirimycin