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通过原位酰亚胺水解扩展二硫键大环库的结构多样性。

Expanding structural diversity in a library of disulfide macrocycles through in-situ imide hydrolysis.

机构信息

Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614, Poznań, Poland.

Center for Advanced Technology, Adam Mickiewicz University, Uniwersytetu Poznańskiego 10, 61-614, Poznań, Poland.

出版信息

Sci Rep. 2022 Jan 7;12(1):38. doi: 10.1038/s41598-021-03944-y.

DOI:10.1038/s41598-021-03944-y
PMID:34997018
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8742088/
Abstract

We describe here an unorthodox approach to dynamic covalent chemistry in which the initially-unexpected in-situ hydrolysis of a bis-imide is employed to control the composition of a library of structurally diverse macrocycles. A single building block is used to generate a library of numerous disulfide-based architectures in a one-pot single-step process. The dual-stimuli method is based on simultaneous changes in pH and DMSO concentration to expand the structural diversity of the macrocyclic products. Mechanistic details of this complex process are investigated by the kinetics analysis. We delivered a facile strategy for the synthesis of water-soluble, multicomponent and dynamic macrocycles equipped with number of different functional groups, thus giving a prospect of their application in guest-driven phase transfer.

摘要

我们在这里描述了一种非传统的动态共价化学方法,其中双酰亚胺的原位水解被用于控制结构多样的大环文库的组成。使用单个构建块在一锅一步法中生成基于二硫键的众多架构文库。双刺激方法基于 pH 和 DMSO 浓度的同时变化来扩展大环产物的结构多样性。通过动力学分析研究了这个复杂过程的机制细节。我们提供了一种简便的策略来合成水溶性、多组分和动态大环,这些大环带有许多不同的官能团,从而为它们在客体驱动的相转移中的应用提供了前景。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/4a49c77e243c/41598_2021_3944_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/00e1992060c8/41598_2021_3944_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/17a9946a273a/41598_2021_3944_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/92439c181530/41598_2021_3944_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/88ae8f99d560/41598_2021_3944_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/a133db8ed5ac/41598_2021_3944_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/4a49c77e243c/41598_2021_3944_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/00e1992060c8/41598_2021_3944_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/17a9946a273a/41598_2021_3944_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/92439c181530/41598_2021_3944_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/88ae8f99d560/41598_2021_3944_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/a133db8ed5ac/41598_2021_3944_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e66e/8742088/4a49c77e243c/41598_2021_3944_Fig6_HTML.jpg

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Dynamic Covalent Chemistry as a Facile Route to Unusual Main-Group Thiolate Assemblies and Disulfide Hoops and Cages.
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Tuning the Solubility of Self-Assembled Fluorescent Aromatic Cages Using Functionalized Amino Acid Building Blocks.使用功能化氨基酸构建块调节自组装荧光芳香笼的溶解度。
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