Synthesis of fluorescence-labelled disaccharide substrates of glucosidase II

被引:17
作者
Cumpstey, I
Butters, TD
Tennant-Eyles, RJ
Fairbanks, AJ
France, RR
Wormald, MR
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Univ Oxford, Glycobiol Inst, Dept Biochem, Oxford OX1 3QU, England
基金
英国工程与自然科学研究理事会;
关键词
glucosidase II; glycoprotein processing; n-pentenyl glycosides; fluorescence labels; N-PENTENYL GLYCOSIDES; LINKED OLIGOSACCHARIDES; 2-AMINOBENZAMIDE; GLYCOSYLATION; CHROMATOGRAPHY; GLYCOPROTEIN; BIOSYNTHESIS; HYDROLYSIS; CALNEXIN; CLONING;
D O I
10.1016/S0008-6215(03)00255-6
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The fluorescence-labelled disaccharides Glcalpha(1-->3)GlcalphaOR and Glcalpha(l-->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. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1937 / 1949
页数:13
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