3-Methoxy-4-(2-nitrovinyl)phenyl glycosides as potential chromogenic substrates for the assay of glycosidases.
Selective glycosidation of 2,4-dihydroxybenzaldehyde with either 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide, 2-acetamido-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride, or 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide afforded the corresponding 4-O-glycosyl derivatives. Subsequent O-methylation, O-deacetylation, and condensation with nitromethane afforded the appropriate beta-glycoside of 3-methoxy-4-(2-nitrovinyl)phenol. The phenol is highly coloured at alkaline pH so that these glycosides may be suitable as chromogenic substrates for the assay of glycosidases.
D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D002863:Chromogenic Compounds; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D009574:Nitro Compounds / Q000138:chemical synthesis; D009904:Optical Rotation; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D014753:Vinyl Compounds / Q000138:chemical synthesis
D002863:Chromogenic Compounds; D006027:Glycosides; D007202:Indicators and Reagents; D009574:Nitro Compounds; D014753:Vinyl Compounds; D006026:Glycoside Hydrolases