有机化学 ›› 2009, Vol. 29 ›› Issue (9): 1317-1324. 上一篇    下一篇

综述与进展

唾液酸糖苷化反应研究新进展

梁芬芬 陈 力 邢国文*   

  1. (北京师范大学化学学院 北京 100875)
  • 收稿日期:2008-09-02 修回日期:2008-12-26 发布日期:2009-12-30
  • 通讯作者: 邢国文

Recent Advances in Sialylation

Liang, Fenfen Chen, Li Xing, Guowen*   

  1. (College of Chemistry, Beijing Normal University, Beijing 100875)
  • Received:2008-09-02 Revised:2008-12-26 Published:2009-12-30
  • Contact: Xing, Guowen

唾液酸是一类重要的具有多种生物学功能的糖酸化合物. 唾液酸糖苷化反应条件较一般糖苷化反应苛刻, 立体选择性通常较差, 端基碳的立体构型较难控制. 在唾液酸糖苷化反应中能否高效地得到α糖苷键是评价该反应优劣的重要标志之一. 唾液酸苷化方法的研究一般涉及以下几个方面: C-2上的离去基团的运用, C-1, C-3上辅助基团的参与作用, C-5上氨基保护基团的修饰, 以及一些新的糖苷化反应催化剂的发展. 近些年来, 这些研究领域, 尤其是C-5上氨基保护基团的研究, 取得了重要进展. 将着重对唾液酸糖苷化方法的新进展做一总结和评述.

关键词: 唾液酸, 糖苷化反应, 噁唑烷酮

Sialic acid is a kind of important sugar acid compound, which has many biological functions. The reaction conditions of sialylation reactions are harsher than the common glycosylation reactions, the stereoselectivities are usually poor, and the configuration of anomeric carbon is difficult to control. Whether α glycosidic bond can be constructed efficiently in sialylation reactions is one of the important criteria to evaluate the reaction quality. Study of sialylation methods generally relates to following areas: the use of different leaving groups at C-2, participation of auxiliary groups at C-1 and C-3, the modification of protec-tive group of NHAc at C-5 and the development of some new promoters. In recent years, these research ar-eas, especially the study of protective group of NHAc at C-5, have made important progress. Herein, we pre-dominately make a summary and review on the new progress of sialylation methods.

Key words: glycosylation, oxazolidone, sialic acid