循环硫酸盐和循环二硫酸盐选择性交联硫酸盐,同时避免单独硫酸盐的修改
Daniel P Donnelly1,2, Matthew G Dowgiallo1, Joseph P Salisbury1,2
1Department of Chemistry and Chemical Biology , Northeastern University , 360 Huntington Avenue , Boston , Massachusetts 02115 , United States.
Journal of the American Chemical Society
|June 1, 2018
概括
新的循环硫酸盐提供精确的醇交叉链接,避免有毒的副产品,并使高效的宏分子研究和聚合物合成成为可能. 这些强大的,细胞透的交叉连接剂在生物条件下有效地发挥作用.
科学领域:
- 化学生物学
- 有机化学
- 生物化学
背景情况:
- 当代的醇选择性交叉链接剂通常会导致有毒的"死胡同"修改.
- 这些不必要的副产品使宏分子结构研究和聚合物合成复杂化.
研究的目的:
- 开发用于选择性醇交联的新型化学工具.
- 通过最大限度地减少死胡同的修改来克服现有的交叉连接剂的局限性.
主要方法:
- 使用铜/超氧化物脱酶 (SOD1) 的二醇对进行测试.
- 使用密度函数理论 (DFT) 计算来理解反应机制.
- 合成了五至七个环状硫酸盐.
主要成果:
- 循环二硫化物,如脂酸,表现出有效的二醇对交叉连接,没有死结产物.
- 与循环二硫化物相比,单-S-oxo衍生物 (循环二硫化物) 的交联速度提高了10^4倍.
- 新的硫酸盐交叉连接剂在氨酸的存在下表现出细胞透性,效能和功能.
结论:
- 循环硫酸盐是一种新型高效的选择性硫酸盐交叉连接剂.
- 这些化合物表现出类似点击的属性,包括高产量,直角性和水相容性.
- 开发的交叉链接剂适用于细胞内应用和先进的聚合物合成.
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