Allosteric Recognition of Homomeric and Heteromeric Pairs of Monosaccharides by a Foldamer Capsule

Mateus, Pedro; Chandramouli, Nagula; Mackereth, Cameron D.; Kauffmann, Brice; Ferrand, Yann; Huc, Ivan

doi:10.1002/ange.201914929

Cited by 15 publications

(3 citation statements)

References 60 publications

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“…They can form 8-, 10-, 12-, and 14-helices, depending on the monomer structure guided by the formation of the hydrogen bonds, responsible for structure formation [ 150 , 164 , 165 ]. The secondary structure of foldamers can be fitted to particular molecules, forming capsules to size [ 166 , 167 ]. The improved structural stability of foldamers can be achieved by intramolecular side-chain crosslinking, providing good material stability [ 168 ].…”

Section: Foldamers In Sensingmentioning

confidence: 99%

Shaping Macromolecules for Sensing Applications—From Polymer Hydrogels to Foldamers

et al. 2022

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Sensors are tools for detecting, recognizing, and recording signals from the surrounding environment. They provide measurable information on chemical or physical changes, and thus are widely used in diagnosis, environment monitoring, food quality checks, or process control. Polymers are versatile materials that find a broad range of applications in sensory devices for the biomedical sector and beyond. Sensory materials are expected to exhibit a measurable change of properties in the presence of an analyte or a stimulus, characterized by high sensitivity and selectivity of the signal. Signal parameters can be tuned by material features connected with the restriction of macromolecule shape by crosslinking or folding. Gels are crosslinked, three-dimensional networks that can form cavities of different sizes and forms, which can be adapted to trap particular analytes. A higher level of structural control can be achieved by foldamers, which are macromolecules that can attain well-defined conformation in solution. By increasing control over the three-dimensional structure, we can improve the selectivity of polymer materials, which is one of the crucial requirements for sensors. Here, we discuss various examples of polymer gels and foldamer-based sensor systems. We have classified and described applied polymer materials and used sensing techniques. Finally, we deliberated the necessity and potential of further exploration of the field towards the increased selectivity of sensory devices.

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Section: Foldamers In Sensingmentioning

confidence: 99%

Shaping Macromolecules for Sensing Applications—From Polymer Hydrogels to Foldamers

et al. 2022

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“…Carbohydrate is a critical component in various biological processes, [1,2] such as energy storage, intercellular communication, and immune response. Synthetic receptors [3][4][5][6][7][8][9][10][11] that bind carbohydrates have the potential to facilitate the investigation of their biological functions and the creation of new therapeutic and diagnostic agents, such as anti-infective agents, synthetic antibodies, and carbohydrate sensors. The development of synthetic receptors [12][13][14] for glucose, in particular, holds significant implications for managing blood glucose levels in diabetes.…”

Section: Introductionmentioning

confidence: 99%

Dynamic Approach to Synthetic Lectin for Glucose with Boosted Binding Affinity through C−H Hydrogen Bonds

Zhai

Cui

et al. 2023

Chemistry A European J

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A biomimetic receptor for glucose has been developed with high affinity and selectivity. The receptor was efficiently synthesized in three steps through dynamic imine chemistry followed by imine‐to‐amide oxidation. The receptor features two parallel durene panels, forming a hydrophobic pocket for [CH⋅⋅⋅π] interactions, and two pyridinium residues directing four amide bonds towards the pocket. These pyridinium residues not only improve solubility but also provide polarized C−H bonds for hydrogen bonding. Experimental data and DFT calculations show that these polarized C−H bonds significantly enhance substrate binding. These findings demonstrate the power of dynamic covalent chemistry for creating molecular receptors and using polarized C−H bonds for boosted carbohydrate recognition in water, providing a foundation for developing glucose‐responsive materials and sensors.

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“…[6] Alternatively,s upramolecular chirality and chiral assemblies could be visualized by means of single crystal X-ray diffraction, which provides ar ather precise determination of chiral assembly and supramolecular chirality. [7][8][9][10][11] Over the past decades,m any self-assembled chiral structures in solid-state have been reported, such as foldamers, [7] helicates, [8] chiral metal-organic polyhedrals/clusters, [9] helical structures [10,11] and double-strand helices. [12,13] These well-defined chiral structures,e ither remaining discrete state or noncovalently bonded with adjacent molecules,a re significantly depending on the specific molecular topology,w hich requires rather delicate design or serendipitous finding.…”

Section: Introductionmentioning

confidence: 99%

Multi‐Modal Chiral Superstructures in Self‐Assembled Anthracene‐Terminal Amino Acids with Predictable and Adjustable Chiroptical Activities and Color Evolution

Wang

Hao

et al. 2020

Angew Chem Int Ed

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Deep understanding of structure–property relationship between packing of chiral building units and their chiroptical behaviors would significantly facilitate the rational design and fabrication of the emerging chiroptical materials such as circularly polarized luminescence (CPL) emissive materials. In this paper, we unveil the universal existence of supramolecular tilt helical superstructures in self‐assembled π‐conjugated amino acid derivatives. A series of coded amino acid methyl esters were conjugated to anthracene segments at N‐terminus, which afforded 21 and 31 symmetry supramolecular tilt chirality in solid‐states. Helical assemblies enabled diversified Cotton effects and CPL performances, which were in accordance with the tilted chirality between anthracene segments. Such correlation shows fine universality, whereby the chiroptical prediction could be realized. Furthermore, on top of charge‐transfer complexation, manipulation of CPL emission colors and handedness were realized.

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Allosteric Recognition of Homomeric and Heteromeric Pairs of Monosaccharides by a Foldamer Capsule

Cited by 15 publications

References 60 publications

Shaping Macromolecules for Sensing Applications—From Polymer Hydrogels to Foldamers

Shaping Macromolecules for Sensing Applications—From Polymer Hydrogels to Foldamers

Dynamic Approach to Synthetic Lectin for Glucose with Boosted Binding Affinity through C−H Hydrogen Bonds

Multi‐Modal Chiral Superstructures in Self‐Assembled Anthracene‐Terminal Amino Acids with Predictable and Adjustable Chiroptical Activities and Color Evolution

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