Synthesis of fluorescence-labelled disaccharide substrates of glucosidase II.
The fluorescence-labelled disaccharides Glcalpha(1-->3)GlcalphaOR and Glcalpha(1-->3)ManalphaOR, both substrates for the glycoprotein-processing enzyme glucosidase II, were synthesised via the use of a n-pentenyl-derived linker at the anomeric position. This allowed incorporation of a pyrenebutyric acid label, via a sequence of oxidative hydroboration, mesylation, azide displacement, reduction with concomitant global deprotection, and peptide coupling. Selective activation of a fully armed thioglycoside in the presence of n-pentenyl glycosides was readily achieved by the use of methyl triflate as promoter.
D000818:Animals; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D005453:Fluorescence; D008099:Liver / Q000378:metabolism; D008969:Molecular Sequence Data; D015394:Molecular Structure; D051381:Rats; D000520:alpha-Glucosidases / Q000378:metabolism*
D004187:Disaccharides; C034251:4-nitrophenyl-alpha-glucosidase; D000520:alpha-Glucosidases