糖基-1H-1,2,3-三唑的合成及生物活性。
Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles.
机构信息
Centre of Biocatalysis and Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídenská 1083, CZ 14220, Prague, Czech Republic.
出版信息
Bioorg Med Chem Lett. 2010 Jul 15;20(14):4263-5. doi: 10.1016/j.bmcl.2010.04.151. Epub 2010 May 15.
Glycosyl 1,2,3-triazoles with alpha-D-gluco, beta-D-gluco, alpha-D-galacto, beta-D-galacto and beta-2-acetamido-2-deoxygluco (GlcNAc) stereochemistry were prepared by reaction of the corresponding azides with vinyl acetate under microwave irradiation. The deprotected glucosyl and galactosyl triazoles did not display inhibitory activity against the tested glycosidases at 1 mM. Of the four fungal glycosidases evaluated, GlcNAc-triazole was found to be hydrolyzed by Talaromyces flavus CCF 2686 beta-N-acetylhexosaminidase. Beta-GlcNAc-triazole was furthermore established to act as a strong ligand of rat and human natural killer cell activating receptors.
具有α-D-吡喃葡萄糖、β-D-吡喃葡萄糖、α-D-半乳糖、β-D-半乳糖和β-2-乙酰氨基-2-脱氧吡喃葡萄糖（GlcNAc）立体化学结构的糖基 1,2,3-三唑通过相应的叠氮化物与醋酸乙烯酯在微波辐射下反应制备。脱保护的葡萄糖基和半乳糖基三唑在 1mM 时对测试的糖苷酶没有显示抑制活性。在所评估的四种真菌糖苷酶中，发现 Talaromyces flavus CCF 2686β-N-乙酰己糖胺酶水解 GlcNAc-三唑。此外，β-GlcNAc-三唑被确定为大鼠和人自然杀伤细胞激活受体的强配体。
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