Reck F
Research Institute, Hospital for Sick Children, Toronto, Ontario, Canada.
Carbohydr Res. 1995 Oct 23;276(2):321-35. doi: 10.1016/0008-6215(95)00183-t.
The C-5 substituted uridine derivatives UDP-5-propylamine (7) and UDP-GlcNAc-5-propylamine (8) were synthesized in good yields by Heck alkylation of the 5-mercuriuridines, followed by hydrogenation. The products were characterized by 1H and 13C NMR spectroscopy, electrospray mass spectrometry and UV spectrophotometry. The amines are of interest for the preparation of affinity probes for glycosyltransferases. The benzoylbenzamides of 7 and 8 show strong competitive inhibition of N-acetylglucosaminyltransferase I and II with Ki values ranging from 30 to 100 microM (without irradiation) and may be useful as active site-directed photoaffinity labels. A conjugate of 8 and Sepharose was used for affinity chromatographic purification of N-acetylglucosaminyltransferases I and II. The results indicate that this affinity gel is a stable alternative to the commonly used but unstable UDP-GlcNAc-5-Hg-thiopropyl conjugate.
通过5-汞代尿苷的Heck烷基化反应，随后进行氢化反应，以良好的产率合成了C-5取代的尿苷衍生物UDP-5-丙胺（7）和UDP-GlcNAc-5-丙胺（8）。通过¹H和¹³C NMR光谱、电喷雾质谱和紫外分光光度法对产物进行了表征。这些胺类对于制备糖基转移酶的亲和探针具有重要意义。7和8的苯甲酰基苯甲酰胺对N-乙酰葡糖胺基转移酶I和II表现出强烈的竞争性抑制作用，其Ki值范围为30至100 μM（无辐射），可能用作活性位点导向的光亲和标记物。8与琼脂糖的缀合物用于N-乙酰葡糖胺基转移酶I和II的亲和色谱纯化。结果表明，这种亲和凝胶是常用但不稳定的UDP-GlcNAc-5-汞代硫丙基缀合物的稳定替代品。
