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Toward Orthogonal Preparation of Sequence-Defined Monodisperse Heteromultivalent Glycomacromolecules on Solid Support Using Staudinger Ligation and Copper-Catalyzed Click Reactions
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2017-09-07 00:00:00 , DOI: 10.1021/acs.joc.7b01398
Tanja Freichel 1 , Svenja Eierhoff 1 , Nicole L. Snyder 2 , Laura Hartmann 1
Affiliation  

The investigation of heteromultivalent interactions of complex glycoligands and proteins is critical for understanding important biological processes and developing carbohydrate-based pharmaceutics. Synthetic glycomimetics, derived by mimicking complex glycoligands on a variety of scaffolds, have become important tools for studying the role of carbohydrates in chemistry and biology. In this paper, we report on a new synthetic strategy for the preparation of monodisperse, sequence-defined glycooligomers or so-called precision glycomacromolecules based on solid phase oligomer synthesis and the Staudinger ligation. This strategy employs a solid-supported synthetic approach using a novel carboxy-functionalized building block which bears a functional handle required for Staudinger ligation on solid support. Furthermore, we combined Staudinger ligation and copper catalyzed azide alkyne cycloaddition (CuAAC) reactions to synthesize heteromultivalent glycooligomers on solid support for the first time, demonstrating the utility of this approach for the synthesis of heterofunctional glycomacromolecules.

中文翻译:

倾向于使用斯托丁格结和铜催化点击反应在固相支持物上正交制备顺序定义的单分散杂多价糖皮质激素

复杂糖配体和蛋白质异多价相互作用的研究对于理解重要的生物过程和开发基于碳水化合物的药物至关重要。通过在多种支架上模拟复杂的糖配体而衍生的合成糖模拟物已成为研究碳水化合物在化学和生物学中的作用的重要工具。在本文中,我们报告了一种基于固相低聚物合成和施陶丁格连接法制备单分散,序列定义的糖低聚物或所谓的精密糖大分子的新合成策略。该策略采用了一种固体支撑的合成方法,该方法使用了一种新型的羧基官能化结构单元,该结构单元具有施陶丁格在固体支撑物上连接所需要的功能性手柄。此外,
更新日期:2017-09-07
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