Carbasugar-thioether pseudodisaccharides related to N-glycan biosynthesis
Carbasugar-thioether pseudodisaccharides related to N-glycan biosynthesis
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DOI：
10.1016/j.carres.2008.12.023
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发表时间：
2009-03-10
影响因子：
3.1
通讯作者：
Butters, Terry D.
中科院分区：
文献类型：
--
作者：
Cumpstey, Ian;Alonzi, Dominic S.;Butters, Terry D.
Analogues of the alpha-Glcp-(1 -> 3)-ot-Glcp and alpha-Glcp-(1 -> 3)-alpha-Manp disaccharides (representing the two alpha-gluco linkages cleaved by alpha-Glucosiclase II in N-glycan biosynthesis) in which the non-reducing-end sugar is replaced by a carbasugar and the inter-glycosidic oxygen by a sulfur were synthesised. The key coupling step was an S(N)2 displacement of an equatorial triflate at C-1 of the carbasugar by C-3 gluco or manno thiolates with inversion of configuration to give thioether pseudodisaccharides with axial substitution at C-1 of the carbasugar. The deprotected pseudodisaccharides failed to inhibit the action of alpha-Glucosidase II as measured both by an in vitro assay and by free oligosaccharide (FOS) analysis from cell studies. (C) 2009 Elsevier Ltd. All rights reserved.
