系统的结构调整产生了酸苏尔顿,用于更快的生物对等蛋白质修饰
Ming Fang1, Gangam Srikanth Kumar1, Qing Lin1
1Department of Chemistry, State University of New York at Buffalo, Buffalo, NY, 14260-3000, USA.
Chembiochem : a European journal of chemical biology
|May 31, 2023
概括
研究人员用CF3组开发了稳定的酸苏顿 (HS),以实现高效的生物结合. 这些化合物在点击化学应用中表现出增强的水稳定性和快速反应性.
科学领域:
- 有机化学 有机化学
- 化学生物学 化学生物学
- 材料科学 材料科学 材料科学
背景情况:
- 酸苏顿 (HS) 是用于点击化学的多功能试剂.
- 提高HS的水稳定性和反应性对于生物应用至关重要.
- 现有的HS通常在水性环境中稳定性有限,这阻碍了它们的使用.
研究的目的:
- 为了合成和表征新型的hydrazonyl sultones (HS) 与一个ortho-CF3组.
- 为了评估这些新的HS化合物的水稳定性和反应性.
- 为了证明HS在与bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN) 的生物结合反应中的实用性.
主要方法:
- 用不同的N-aryl替代剂和不同尺寸的sultone环合成hydrazonyl sultones (HS).
- 在水性条件下 HS 稳定性的表征.
- 在与 BCN 的1,3-双极循环加法反应中对 HS 反应性的研究.
- 进行X射线晶体结构分析以了解稳定性机制.
- 在修改NCB编码的纳米体中的应用.
主要成果:
- 含有ortho-CF3组的新型HS在中等到良好的产量中成功合成.
- X射线结晶学显示,CF3组通过静电屏蔽化物 imine中心,增强水性稳定性.
- 富含电子的六个组成的HS显示出出色的水稳定性和增加的循环添加反应性.
- 在PBS-乙醇中,HS-BCN结合实现了高二次速率常数 (高达1500M-1s-1),证明了快速和选择性的生物结合.
结论:
- орто-CF3 组显著增强了水尼尔苏尔顿的水稳定性.
- N-aryl替代剂和苏环大小调节HS的反应性和稳定性.
- 这些改进的HS试剂使得高效和快速的生物结合成为可能,在化学生物学中推进了应用.
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