O-乙酰氨基半乳糖基化氨基酸的化学合成

Chemical synthesis of building blocks for O linked synthetic glycopeptide

目的 为获得精确定位糖基化糖肽 ,合成O 乙酰氨基半乳糖基化氨基酸 ,作为糖肽固相合成的原料。方法 利用环状糖结构的半缩醛羟基可与含侧链羟基氨基酸的羟基形成糖苷键 ,用化学方法 ,使过乙酰化GalNAc与氨基被 9 Fluorenylmethoxycarbonyl (N α Fmoc)保护的丝氨酸或苏氨酸连接。结果 反应产物通过反相制备HPLC纯化后 ,可作为O 连接糖肽合成构建单位 (Buildingblocks)在固相多肽合成仪上合成所需的病毒或肿瘤相关糖肽 ,并可进一步研究其生物学活性。结论 本法相对易操作 ,重复性好 ,收益率也较高 ,更重要的是糖基化的均一性好 。

Objective To obtain the exactly glycosylated peptide by glycosylated N α Fmoc serine and threonine were synthesized as the raw material for solid phase glycopeptide synthesis. Methods The glycosylation of N α Fmoc serine or threonine with 2 acetamido 2 deoxy D galactose(GalNAc) pentaacetate was carried out with BF3 Et2O and SnCl4 as promoters in CH 2Cl 2 or CH 3CN. Results After purification with reversed phase HPLC, the glycosylated N α Fmoc serine or threonine can be further used as the building blocks to synthesize viral or tumorous glycopeptide with solid phase polypeptide synthesizor. Conclusion This method is easy to perform and with high repeatability and better yield, especially the glycosylation is well distributed.