期刊
CARBOHYDRATE RESEARCH
卷 345, 期 9, 页码 1123-1134出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.03.041
关键词
Click chemistry; alpha-D-Glucopyranosyl azide reactivity; Microwave; Triazole; Glucosidase inhibitor
资金
- UK BBSRC
- University of East Anglia
- BBSRC [BBS/E/J/000C0618] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BBS/E/J/000C0618] Funding Source: researchfish
Cu(I)-catalysed azide alkyne 1,3-dipolar cycloaddition (CuAAC) 'click chemistry' was used to assemble a library of 21 alpha-D- and beta-D-glucopyranosyl triazoles, which were assessed as potential glycosidase inhibitors. In the course of this work, different reactivities of isomeric alpha- and beta-glucopyranosyl azides under CuAAC conditions were noted. This difference was further investigated using competition reactions and rationalised on the basis of X-ray crystallographic data, which revealed significant differences in bond lengths within the azido groups of the alpha- and beta-anomers. Structural studies also revealed a preference for perpendicular orientation of the sugar and triazole rings in both the alpha- and beta-glucosyl triazoles in the solid state. The triazole library was assayed for inhibition of sweet almond beta-glucosidase (GH1) and yeast alpha-glucosidase (GH13), which led to the identification of a set of glucosidase inhibitors effective in the 100 mu M range. The preference for inhibition of one enzyme over the other proved to be dependent on the anomeric configuration of the inhibitor, as expected. (C) 2010 Elsevier Ltd. All rights reserved.
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