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难以捉摸的拉姆诺西尔二氧化离子的表征及其在复杂的寡糖化合物合成中的应用

Peter H Moons¹, Floor Ter Braak¹, Frank F J de Kleijne¹

¹Synthetic Organic Chemistry, Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ, Nijmegen, The Netherlands.

Nature communications

|March 14, 2024

概括

研究人员开发了一种新的工作流程,以表征难以捉摸的糖化中间体,从而实现精确的碳水化合物合成. 这种方法增强了对碳水化合物化学的理解,并有助于制造复杂的寡糖.

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
物理化学物理化学

背景情况:

控制碳水化合物合成中的异构配置仍然是一个重大挑战.
甘氨基酸离子,像氧化碳和二氧化离子一样,是甘氨基化反应中的关键反应中间体.
描述这些中间体对于复杂碳水化合物的立体选择性合成至关重要,但远程参与中间体很难研究.

研究的目的:

开发和应用一种工作流程,用于表征rhamnosyl 1,3-桥接的二氧化离子,难以捉摸的糖基化中间体.
通过计算和光谱方法阐明这些中间体的结构和反应性.
将发现应用于复杂细菌寡糖的合成.

主要方法:

利用量子化学计算和红外离子光谱来确定气相中间结构.
采用先进的核磁共振 (NMR) 技术 (CEST,EXSY,COSY,HSQC,HMBC) 用于溶液相特性和动力学.
在有机合成中应用C-3基邻群参与策略.

主要成果:

成功确定了rhamnosyl 1,3-桥接的二氧化离子的结构.
确定了溶液中高反应性,低丰度物种的结构和交换动力学.
证明了C-3邻组参与合成复杂细菌寡糖的实用性.

结论:

集成的工作流提供了一种可靠的方法来阐明高反应性糖基化中间体.
这种方法将基本的物理化学理解与有机合成中的实际应用联系起来.
推进复杂碳水化合物的立体选择性合成,特别是细菌的寡糖.

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