用于迭代寡糖合成的单氟与二氟标记葡糖胺
Mono- Vs. Di-flourous tagged Glucosamines for Iterative Oligosaccharide Synthesis.
作者信息
Park Gisun, Ko Kwang-Seuk, Zakharova Aleksandra, Pohl Nicola L
机构信息
2756 Gilman, Department of Chemistry and the Plant Sciences Institute, Iowa State University, Ames, IA 50011 USA.
出版信息
J Fluor Chem. 2008 Oct;129(10):978-982. doi: 10.1016/j.jfluchem.2008.05.001.
Fluorous-tagged protecting groups are attractive tools for elongating carbohydrate chains in oligosaccharide synthesis. To eliminate the accumulation of failed sequences during automated oligosaccharide synthesis conditions, an additional C(8)F(17) ester derived protecting group was attached to the glycosyl donor to better retain the desired doubly-tagged glycosylation product on fluorous solid phase extraction (FSPE) cartridges. Initial studies show that the double-fluorous-tagging strategy offers a robust enough separation using a commercial FSPE cartridge using simple gravity filtration to separate the desired product from the singly-fluorous-tagged starting materials and their decomposition products. In addition, removal of the fluorous acetate and its byproducts after sodium methoxide treatment and neutralization required only dissolution of the desired sugar in toluene and subsequent removal of the toluene layer from the denser fluorous byproducts.
含氟标记的保护基团是寡糖合成中延长碳水化合物链的有吸引力的工具。为了消除自动寡糖合成条件下失败序列的积累，一个额外的C(8)F(17)酯衍生保护基团被连接到糖基供体上，以便在含氟固相萃取（FSPE）柱上更好地保留所需的双标记糖基化产物。初步研究表明，双含氟标记策略使用商业FSPE柱，通过简单重力过滤从单含氟标记的起始原料及其分解产物中分离出所需产物，提供了足够稳健的分离效果。此外，在甲醇钠处理和中和后，去除含氟乙酸盐及其副产物只需要将所需的糖溶解在甲苯中，随后从密度较大的含氟副产物中除去甲苯层。
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