A Synthetic Lectin for Glucuronate

IF 10.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Canjia Zhai, , , Chengkai Xu, , , Yunpeng Cui, , , Lukasz Wojtas, , , Jianfeng Cai, , and , Wenqi Liu*, 
{"title":"A Synthetic Lectin for Glucuronate","authors":"Canjia Zhai,&nbsp;, ,&nbsp;Chengkai Xu,&nbsp;, ,&nbsp;Yunpeng Cui,&nbsp;, ,&nbsp;Lukasz Wojtas,&nbsp;, ,&nbsp;Jianfeng Cai,&nbsp;, and ,&nbsp;Wenqi Liu*,&nbsp;","doi":"10.1021/acscentsci.5c00951","DOIUrl":null,"url":null,"abstract":"<p >The selective recognition of hydrophilic carbohydrates in water remains a longstanding challenge in supramolecular chemistry due to solvent competition and the lack of a strong driving force comparable to the hydrophobic effect. Herein, we report the design, synthesis, and characterization of a water-soluble tetralactam macrocycle, MPNT<sup>2+</sup>·2Cl<sup>–</sup>, as a highly effective synthetic lectin for glucuronate. MPNT<sup>2+</sup>·2Cl<sup>–</sup> features two dimethylnaphthalene panels, pyridinium spacers, and morpholine side chains, forming a rigid, preorganized cavity with convergent hydrogen bond donors, polarized C–H donors, and complementary electrostatic interactions. The receptor achieves a binding affinity of 103,000 M<sup>–1</sup> for glucuronate in water, over 19-fold higher than previous synthetic systems, along with excellent selectivity over structurally similar carbohydrates. Single-crystal X-ray analysis, DFT calculation, and IGMH analysis reveal a dense network of [N–H···O], [C–H···O], and [C–H···π] interactions, highlighting the role of stereoelectronic complementarity in complex formation. Moreover, MPNT<sup>2+</sup>·2Cl<sup>–</sup> acts as a chiroptical sensor, producing binding-induced circular dichroism signals that enable sensitive detection of glucuronic acid at physiologically relevant concentrations. This work presents a generalizable strategy for designing synthetic lectins that recognize carbohydrates in aqueous solutions and opens up new possibilities for developing molecular sensors and diagnostic tools for biologically important anionic sugars.</p><p >A synthetic macrocyclic lectin recognizes glucuronate in water, enabling strong, selective binding and chiroptical sensing of a biologically important sugar.</p>","PeriodicalId":10,"journal":{"name":"ACS Central Science","volume":"11 9","pages":"1753–1761"},"PeriodicalIF":10.4000,"publicationDate":"2025-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acscentsci.5c00951","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Central Science","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acscentsci.5c00951","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

The selective recognition of hydrophilic carbohydrates in water remains a longstanding challenge in supramolecular chemistry due to solvent competition and the lack of a strong driving force comparable to the hydrophobic effect. Herein, we report the design, synthesis, and characterization of a water-soluble tetralactam macrocycle, MPNT2+·2Cl, as a highly effective synthetic lectin for glucuronate. MPNT2+·2Cl features two dimethylnaphthalene panels, pyridinium spacers, and morpholine side chains, forming a rigid, preorganized cavity with convergent hydrogen bond donors, polarized C–H donors, and complementary electrostatic interactions. The receptor achieves a binding affinity of 103,000 M–1 for glucuronate in water, over 19-fold higher than previous synthetic systems, along with excellent selectivity over structurally similar carbohydrates. Single-crystal X-ray analysis, DFT calculation, and IGMH analysis reveal a dense network of [N–H···O], [C–H···O], and [C–H···π] interactions, highlighting the role of stereoelectronic complementarity in complex formation. Moreover, MPNT2+·2Cl acts as a chiroptical sensor, producing binding-induced circular dichroism signals that enable sensitive detection of glucuronic acid at physiologically relevant concentrations. This work presents a generalizable strategy for designing synthetic lectins that recognize carbohydrates in aqueous solutions and opens up new possibilities for developing molecular sensors and diagnostic tools for biologically important anionic sugars.

A synthetic macrocyclic lectin recognizes glucuronate in water, enabling strong, selective binding and chiroptical sensing of a biologically important sugar.

葡萄糖醛酸的合成凝集素
由于溶剂竞争和缺乏与疏水效应相媲美的强大驱动力,在水中选择性识别亲水碳水化合物一直是超分子化学领域的一个长期挑战。在这里,我们报道了一种水溶性四内酰胺大环MPNT2+·2Cl -的设计、合成和表征,作为一种高效的葡萄糖醛酸盐凝集素。MPNT2+·2Cl -具有两个二甲基萘面板、吡啶间隔层和啉侧链,形成一个刚性的、预先组织的腔体,具有收敛的氢键供体、极化的碳氢供体和互补的静电相互作用。该受体对葡萄糖醛酸盐在水中的结合亲和力为103,000 M-1,比以前的合成系统高19倍以上,同时对结构相似的碳水化合物具有出色的选择性。单晶x射线分析、DFT计算和IGMH分析揭示了[N-H··O]、[C-H··O]和[C-H··π]相互作用的密集网络,突出了立体电子互补在络合物形成中的作用。此外,MPNT2+·2Cl -作为一种触觉传感器,产生结合诱导的圆二色性信号,使葡萄糖醛酸在生理相关浓度下的敏感检测成为可能。这项工作提出了一种设计可识别水溶液中碳水化合物的合成凝集素的通用策略,并为开发具有重要生物学意义的阴离子糖的分子传感器和诊断工具开辟了新的可能性。合成的大环凝集素可以识别水中的葡萄糖醛酸盐,从而实现对一种生物学上重要的糖的强选择性结合和热带感应。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
ACS Central Science
ACS Central Science Chemical Engineering-General Chemical Engineering
CiteScore
25.50
自引率
0.50%
发文量
194
审稿时长
10 weeks
期刊介绍: ACS Central Science publishes significant primary reports on research in chemistry and allied fields where chemical approaches are pivotal. As the first fully open-access journal by the American Chemical Society, it covers compelling and important contributions to the broad chemistry and scientific community. "Central science," a term popularized nearly 40 years ago, emphasizes chemistry's central role in connecting physical and life sciences, and fundamental sciences with applied disciplines like medicine and engineering. The journal focuses on exceptional quality articles, addressing advances in fundamental chemistry and interdisciplinary research.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信