Cation Molecular Exchanger Based on a Conformational Hinge

Ravi, Anil; Krishnarao, P. Sivarama; Shumilova, Tatiana A.; Khrustalev, Victor N.; Rüffer, Tobias; Lang, Heinrich; Kataev, Evgeny A.

doi:10.1021/acs.orglett.8b02687

Cited by 9 publications

(8 citation statements)

References 41 publications

(61 reference statements)

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“…Chemical signaling using K + ion translocation between the allosteric capture/release system [K(203)] + and receptor 204 was recently described by Kataev (Figure 73). 315 Crown ether 204 displayed a lower affinity for potassium than the allosteric capture/release system 203. Upon addition of 1 equiv of zinc(II) to [K(203)] + , both bipyridine receptor units formed an intramolecular zinc complex which induced a conformational change in both the cyclohexane ring as well as the crown-ether subunit.…”

Section: Metal-ion Triggered Communicationmentioning

confidence: 99%

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(Nano)mechanical Motion Triggered by Metal Coordination: from Functional Devices to Networked Multicomponent Catalytic Machinery

et al. 2019

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A look at the elegance and efficiency of biological machines readily reveals that Nature masters the full gamut of chemical interactions to compose masterpieces of the living world. The present analysis singles out metal coordination for the actuation of nanomechanical motion. According to our analysis, metal coordination has a manifold of rewards, putting it primo loco in opportunities for putting nanomechanical systems into action: (i) its strength and dynamics can be properly modulated and fine-tuned by the choice of metal, redox state, and ligand(s), (ii) the high directionality of the interaction allows reliable design, and (iii) the emergence of novel self-sorting algorithms allows multiple of these interactions to be working in parallel. On top of all these advantages, intermolecular metal-ion translocation is a well-known factor in biological signaling. These benefits have recently proven their usefulness in the operation of networked devices and in overcoming the limitations of traditional stand-alone molecular systems.

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Section: Metal-ion Triggered Communicationmentioning

confidence: 99%

“…Figure 73. Chemical signal transduction between the allosteric capture/release system 203 and receptor 204 315. …”

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confidence: 99%

(Nano)mechanical Motion Triggered by Metal Coordination: from Functional Devices to Networked Multicomponent Catalytic Machinery

et al. 2019

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“…Many of these systems are based on chelation of metal ions to induce a conformational change, e.g., by crown ether moieties . Zn 2+ ions have a strong chelation with 2,2′-bipyridine groups, and this has been used for molecular machines, sensors, and ion exchangers . We therefore proposed that a glycosyl donor protected with two 2,2′-bipyridine groups would possess the same features as a conformational switch.…”

Section: Introductionmentioning

confidence: 99%

Conformationally Switchable Glycosyl Donors

Holmstrøm

Pedersen

2019

J. Org. Chem.

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Glycosyl donors functionalized with 2,2′-bipyridine moieties on the 3-OH and 6-OH or the 2-OH and 4-OH undergo a conformational change when forming 1:1 complexes with Zn2+ ions. The pyranoside ring of the zinc complexes adopted axial-rich skew boat conformations. The reactivities of the two glycosyl donors were investigated by performing a series of glycosylations in the presence or absence of Zn2+ ions. These glycosylations suggested a decrease in reactivity when binding Zn2+. The conformational effect of binding Zn2+ was therefore studied using a third glycosyl donor, unable to undergo conformational changes when binding Zn2+. From competition experiments, it was observed that the binding-induced conformational change increased the reactivity slightly compared to the glycosyl donor unable to undergo a conformational change.

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“…diamino groups coordinating with metal ions when being in the 1,3-diaxial orientation (Scheme 5a). This hinge motion of the trisaccharide analogues (35)(36)(37) can be applied in molecular machine architectures. 7,54,55 'Hinge' sugars, like 2,4-diamino-2,4-dideoxy-xylopyranosides (38), shed light on the use of carbohydrate derivatives as molecular switches, by which all four equatorial substituents can change to an axial orientation through a metal-triggered 4 C 1 to 1 C 4 conformational flip.…”

Section: Short Review Synthesismentioning

confidence: 99%

Ring-System-Based Conformational Switches and their Applications in Sensing and Liposomal Drug Delivery

Pedersen

2022

Synthesis

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In the past decades, a great number of stimuli-responsive systems have been developed to be used as drug-delivery systems with high sensitivity and selectivity in targeted therapy. Despite promising results, the current stimuli-responsive systems suffer from the complexity of preparation, as most novel stimuli-responsive systems are based on polymers. Small molecules have often been neglected as candidates for application for stimuli-responsive systems. Recently, structures based on six-membered ring molecules or bicyclic molecules have been developed into conformational switches working through conformational interconversion. These single conformational switches have significantly reduced the complexity of material preparation compared to polymers or copolymers. In this review, we focus on ring-system-based conformational switches that are involved in sensors and smart drug-delivery systems. We hope that this review will shed light on ring-system-based single conformational switches for use in the development of stimuli-responsive systems.1 Introduction2 Conformation Switches Based On Bispidine Derivatives3 Conformation Switches Based On Cycloalkanes4 Conformation Switches Based On Carbohydrates5 Conclusion

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Cation Molecular Exchanger Based on a Conformational Hinge

Cited by 9 publications

References 41 publications

(Nano)mechanical Motion Triggered by Metal Coordination: from Functional Devices to Networked Multicomponent Catalytic Machinery

(Nano)mechanical Motion Triggered by Metal Coordination: from Functional Devices to Networked Multicomponent Catalytic Machinery

Conformationally Switchable Glycosyl Donors

Ring-System-Based Conformational Switches and their Applications in Sensing and Liposomal Drug Delivery

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