{"title":"用于驯服草酸盐的定制电荷中性自组装 L2Zn2 容器。","authors":"David Ocklenburg, David Van Craen","doi":"10.3762/bjoc.20.250","DOIUrl":null,"url":null,"abstract":"<p><p>Dicarboxylic acids and their derivatives play crucial roles in various biological processes, necessitating the development of effective receptors for their detection. In particular, the smallest dicarboxylate, oxalate, presents a significant importance due to its widespread presence in nature and its association with various diseases. Yet, very little attention was devoted to the recognition of oxalate with metal-driven self-assemblies like cages or containers while numerous classic organic receptors for oxalate exist. This discrepancy is astonishing because metallocontainers or metallocages have advantages over classic macrocycles or organocages like a higher modularity and good preorganization paired with a ready receptor preparation by metal complexation. The reason for the underrepresentation is the competitive nature and excellent ligand properties of oxalate which not only is associated with the aforementioned diseases but also poses a serious hazard for metal-driven self-assemblies because the dianion can easily replace ligand strands leading to a partial or full receptor decomposition. Herein, we present a charge-neutral zinc(II)-based metallocontainer which was tuned to contest oxalate as most competitive dicarboxylate. The dianion is bound in a 1:1 fashion with a binding constant of log <i>K</i> = 4.39 selectively over other dicarboxylates by maintaining the receptor stability. This study highlights the importance of a highly modular receptor design so that tailored hosts can be designed to tackle the recognition of challenging competitive analytes.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"3007-3015"},"PeriodicalIF":2.2000,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11590019/pdf/","citationCount":"0","resultStr":"{\"title\":\"Tailored charge-neutral self-assembled L<sub>2</sub>Zn<sub>2</sub> container for taming oxalate.\",\"authors\":\"David Ocklenburg, David Van Craen\",\"doi\":\"10.3762/bjoc.20.250\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Dicarboxylic acids and their derivatives play crucial roles in various biological processes, necessitating the development of effective receptors for their detection. In particular, the smallest dicarboxylate, oxalate, presents a significant importance due to its widespread presence in nature and its association with various diseases. Yet, very little attention was devoted to the recognition of oxalate with metal-driven self-assemblies like cages or containers while numerous classic organic receptors for oxalate exist. This discrepancy is astonishing because metallocontainers or metallocages have advantages over classic macrocycles or organocages like a higher modularity and good preorganization paired with a ready receptor preparation by metal complexation. The reason for the underrepresentation is the competitive nature and excellent ligand properties of oxalate which not only is associated with the aforementioned diseases but also poses a serious hazard for metal-driven self-assemblies because the dianion can easily replace ligand strands leading to a partial or full receptor decomposition. Herein, we present a charge-neutral zinc(II)-based metallocontainer which was tuned to contest oxalate as most competitive dicarboxylate. The dianion is bound in a 1:1 fashion with a binding constant of log <i>K</i> = 4.39 selectively over other dicarboxylates by maintaining the receptor stability. This study highlights the importance of a highly modular receptor design so that tailored hosts can be designed to tackle the recognition of challenging competitive analytes.</p>\",\"PeriodicalId\":8756,\"journal\":{\"name\":\"Beilstein Journal of Organic Chemistry\",\"volume\":\"20 \",\"pages\":\"3007-3015\"},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2024-11-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11590019/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Beilstein Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.3762/bjoc.20.250\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/1/1 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.20.250","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
二羧酸及其衍生物在各种生物过程中发挥着至关重要的作用,因此有必要开发有效的受体来检测它们。尤其是最小的二羧酸盐草酸盐,由于其在自然界中的广泛存在以及与各种疾病的关联,其重要性不言而喻。然而,人们很少关注用金属驱动的自组装(如笼子或容器)来识别草酸盐,而草酸盐的经典有机受体却层出不穷。这种差异令人吃惊,因为金属容器或金属锁链与传统的大环或有机锁链相比具有更高的模块性和良好的预组织性,并可通过金属络合随时制备受体等优势。草酸盐具有竞争性和优良的配体特性,不仅与上述疾病相关,而且对金属驱动的自组装构成严重危害,因为二价离子很容易取代配体链,导致部分或全部受体分解。在此,我们介绍了一种电荷中性的锌(II)基金属容器,该容器经调整后可与草酸盐竞争,成为最具竞争力的二羧酸盐。通过保持受体的稳定性,该二元离子以 1:1 的方式与对数 K = 4.39 的结合常数选择性地与其他二羧酸盐结合。这项研究强调了高度模块化受体设计的重要性,这样就可以设计出定制的宿主来识别具有挑战性的竞争性分析物。
Tailored charge-neutral self-assembled L2Zn2 container for taming oxalate.
Dicarboxylic acids and their derivatives play crucial roles in various biological processes, necessitating the development of effective receptors for their detection. In particular, the smallest dicarboxylate, oxalate, presents a significant importance due to its widespread presence in nature and its association with various diseases. Yet, very little attention was devoted to the recognition of oxalate with metal-driven self-assemblies like cages or containers while numerous classic organic receptors for oxalate exist. This discrepancy is astonishing because metallocontainers or metallocages have advantages over classic macrocycles or organocages like a higher modularity and good preorganization paired with a ready receptor preparation by metal complexation. The reason for the underrepresentation is the competitive nature and excellent ligand properties of oxalate which not only is associated with the aforementioned diseases but also poses a serious hazard for metal-driven self-assemblies because the dianion can easily replace ligand strands leading to a partial or full receptor decomposition. Herein, we present a charge-neutral zinc(II)-based metallocontainer which was tuned to contest oxalate as most competitive dicarboxylate. The dianion is bound in a 1:1 fashion with a binding constant of log K = 4.39 selectively over other dicarboxylates by maintaining the receptor stability. This study highlights the importance of a highly modular receptor design so that tailored hosts can be designed to tackle the recognition of challenging competitive analytes.
期刊介绍:
The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry.
The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.