{"title":"Dynamic Cyclodipeptide Clamps as Enantioselective Receptors toward Vitamin K1.","authors":"Zhuoer Wang, Yitong Gai, Aiyou Hao, Pengyao Xing","doi":"10.1021/acs.nanolett.5c02793","DOIUrl":null,"url":null,"abstract":"<p><p>We report the design of folded cyclodipeptides that show dynamic and adaptive conformational transitions responding to solvents and enantioselective recognition of a biomolecule, vitamin K1 (VK1). Postmodification of phenylalanine-based cyclodipeptides with polycyclic aromatic hydrocarbons (pyrene, anthracene, and phenanthrene) produced chiral folded structures. Compared with other solvents, these cyclodipeptides exhibit ultrahigh sensitivity to dimethyl sulfoxide (DMSO), which induces a conformational transition from parallel to perpendicular dimerization. It leads to a reversed screw sense of the chromophores, facilitating tunable chiroptical properties. In a mixed DMSO/water system, the folded cyclodipeptides perform as efficient molecular clamps that recognize VK1 through charge-transfer complexation. Additionally, d,d- and l,l-configured cyclodipeptides displayed enantioselective recognition of VK1, as evidenced by differences in binding affinity, circularly polarized luminescence and self-assembled nanoarchitectures. This study provides approaches for artificial receptors and chiral sensing based on cyclopeptides.</p>","PeriodicalId":53,"journal":{"name":"Nano Letters","volume":" ","pages":""},"PeriodicalIF":9.6000,"publicationDate":"2025-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Nano Letters","FirstCategoryId":"88","ListUrlMain":"https://doi.org/10.1021/acs.nanolett.5c02793","RegionNum":1,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
We report the design of folded cyclodipeptides that show dynamic and adaptive conformational transitions responding to solvents and enantioselective recognition of a biomolecule, vitamin K1 (VK1). Postmodification of phenylalanine-based cyclodipeptides with polycyclic aromatic hydrocarbons (pyrene, anthracene, and phenanthrene) produced chiral folded structures. Compared with other solvents, these cyclodipeptides exhibit ultrahigh sensitivity to dimethyl sulfoxide (DMSO), which induces a conformational transition from parallel to perpendicular dimerization. It leads to a reversed screw sense of the chromophores, facilitating tunable chiroptical properties. In a mixed DMSO/water system, the folded cyclodipeptides perform as efficient molecular clamps that recognize VK1 through charge-transfer complexation. Additionally, d,d- and l,l-configured cyclodipeptides displayed enantioselective recognition of VK1, as evidenced by differences in binding affinity, circularly polarized luminescence and self-assembled nanoarchitectures. This study provides approaches for artificial receptors and chiral sensing based on cyclopeptides.
期刊介绍:
Nano Letters serves as a dynamic platform for promptly disseminating original results in fundamental, applied, and emerging research across all facets of nanoscience and nanotechnology. A pivotal criterion for inclusion within Nano Letters is the convergence of at least two different areas or disciplines, ensuring a rich interdisciplinary scope. The journal is dedicated to fostering exploration in diverse areas, including:
- Experimental and theoretical findings on physical, chemical, and biological phenomena at the nanoscale
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