使用甘酸和滴酸试剂作为甘化剂的寡糖糖化物合成
O J Plante1, E R Palmacci, R B Andrade
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Journal of the American Chemical Society
|September 27, 2001
概括
这项研究介绍了一种高效的单合成甘氨酸酸盐和dithiophosphates从glycals. 这些化合物作为多用途的甘氨基基捐赠体,用于创建多样化的甘氨基酸链接,对于寡糖组装至关重要.
科学领域:
- 碳水化合物化学 碳水化合物化学
- 有机合成 有机合成
- 葡萄糖科学 (Glycoscience) 是一种科学.
背景情况:
- 甘氨酸酸盐是碳水化合物化学中的关键中间体.
- 多种葡萄糖酸结合物的高效合成对于寡糖的构造至关重要.
研究的目的:
- 开发一台高效的alpha-和beta-glycosyl酸盐和dithiophosphate试验器的一合成.
- 为了探索它们作为多用途的甘氨基基捐赠体,用于各种甘氨基化反应的实用性.
- 建立直角和区域选择性糖化策略.
主要方法:
- 通过1,2-无水糖从糖中合成糖酸和二酸的一合成.
- 用三甲基三甲硫酸盐 (TMSOTf) 激活甘酸酸盐.
- 酸催化合与化受体. 酸催化合与化受体.
- 坐标和区域选择性糖化策略.
主要成果:
- 阿尔法和β-糖酸和dithiophosphate试剂的高效合成.
- 成功的O-,S-和C-糖化,形成β-葡萄糖酸,β-银酸,α-酸,α-曼诺酸,β-葡萄糖酸和β-葡萄糖胺链接.
- 已证明与含有糖醇的受体的兼容性,用于β-糖化的形成.
- 发展直角和区域选择性糖化方法.
结论:
- 甘氨基酸盐和滴氨基酸盐是多功能甘氨基酸的捐赠者.
- 开发的方法可以有效地组装复杂的寡糖.
- 这些策略尽量减少保护群体操纵,并提供区域化学控制.
相关概念视频
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