在糖基化反应中利用自由硫酸盐组
Yuta Maki1,2, Akihiro Manbo1, Junpei Abe1
1Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, 560-0043, Toyonaka, Osaka, Japan.
Angewandte Chemie (International ed. in English)
|November 14, 2024
概括
合成硫酸寡糖是非常具有挑战性的. 这项研究表明,使用特定的激活组和或盐,用自由硫酸盐组进行糖化是可行的,简化了合成.
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:
- 传统的硫化寡糖合成涉及保护硫酸盐组或硫化后.
- 在甘氨基化过程中自由硫酸盐群的行为仍然不太清楚.
研究的目的:
- 为了研究使用自由硫酸盐组进行糖基化反应的可行性.
- 确定有效的激活组和合成硫酸寡糖的反应条件.
主要方法:
- 检查了各种具有自由硫酸盐群的甘氨基基捐赠体.
- 使用2-N-trifluoroacetyl (2-NTroc) 和2-O-acetyl组进行激活.
- 研究了不同对抗离子 (Na +,Li +,K +,Ba2 +,pyridinium) 对糖化酶的影响.
- 进行了ab initio计算以支持反应机制.
- 在分糖酸供体-接受体对之间进行了糖化反应.
主要成果:
- 含有自由硫酸盐群的糖胺基和硫酸盐基是没有成功的.
- 用2-NTroc或2-O-乙烯基组激活6硫酸的GalNAc供体,可以有效地产生β-糖化物.
- 邻近组参与是有效的,即使没有保护的硫酸盐组.
- 和盐捐赠者提供了良好的产量.
- 硫酸四糖从二糖前体中成功合成.
- 最初的计算支持了提出的反应机制和的作用.
结论:
- 可以与自由硫酸盐群进行直接糖基化.
- 特定的激活基和对抗基 (Na+,Li+) 对于成功至关重要.
- 盐可以在糖化过程中作为保护组,简化合成策略.
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