Synthesis of fluorescence-labelled disaccharide substrates of glucosidase II |
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Authors: | Cumpstey Ian Butters Terry D Tennant-Eyles Richard J Fairbanks Antony J France Robert R Wormald Mark R |
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Affiliation: | Dyson Perrins Laboratory, Oxford University, South Parks Road, Oxford OX1 3QY, UK. |
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Abstract: | 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. |
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Keywords: | Glucosidase II Glycoprotein processing n-Pentenyl glycosides Fluorescence labels |
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