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对自动化固相寡核酸合成的bicyclo[6.1.0]nonyne支架的合成和稳定性研究

Kristina Karalė^1,2, Martin Bollmark², Antanas Karalius²

¹Department of Biosciences and Nutrition, Karolinska Institutet Neo 141 57 Huddinge Sweden kristina.karale@ri.se.

|May 30, 2024

概括

合成了两种新型的双循环[6.1.0]无名 (BCN) 链接剂,用于直接的寡核酸结合. 这些BCN衍生物在酸性条件下表现出稳定性,并且在应变促进的基酸循环添加反应中有效.

科学领域:

有机化学有机化学
生物结合化学生物结合化学
氧核酸合成的合成方法

背景情况:

应变促进的酸循环添加 (SPAAC) 是一种对生物结合至关重要的生物对等反应.
将活性链接剂纳入寡核酸中需要与自动化固相合成相容的方法.
现有的寡核酸修饰方法可能在稳定性或反应效率方面存在局限性.

研究的目的:

开发用于寡核酸合成的新型双[6.1.0]无 (BCN) 链接子衍生物.
在酸性条件下评估这些NCB衍生品和由此产生的寡核酸的稳定性.
评估SPAAC反应中的衍生 BCN链接器的反应性.

主要方法:

标准自动化固相合成用于将 BCN 链接子衍生物纳入寡核酸序列.
在各种酸性条件下对 BCN-carbinol 和 BCN-oligonucleotides 进行了稳定性研究.
使用非酸性和酸性处理的BCN链接剂进行了应变促进的酸循环添加 (SPAAC) 反应.

主要成果:

两种新型的 BCN 链接子衍生物已成功合成并纳入寡核酸中.
当暴露在酸性条件下时, BCN-carbinol和 BCN-oligonucleotides表现出稳定性.
衍生 BCN 链接剂,无论酸处理如何,都有效地参与了 SPAAC 反应.

结论:

开发的 BCN 链接子衍生物适合通过自动合成直接纳入寡核酸.
这些 BCN 连接器在酸性条件下提供了良好的稳定性,在各种化学环境中扩大了它们的实用性.
在SPAAC反应中,BCN链接器是有效的,使改性寡核酸的有效生物结合成为可能.

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