Biomimetic carbohydrate recognition

Davis, Anthony P.

doi:10.1039/c9cs00391f

Cited by 117 publications

(165 citation statements)

References 55 publications

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“…Externally‐directed charged groups (positive or negative) are thus common features (Figure 3 ). Dendrimeric units can be especially effective, [20] and have figured prominently in our own work [21] …”

Section: Design and Synthesis Of Receptors For Studies In Watermentioning

confidence: 93%

“…D endrimeric units can be especially effective, [20] and have figured prominently in our own work. [21] Ther eceptor core will need to provide preorganised hydrogen bonding groups which complement those on the target as precisely as possible.G enerally these will be presented within ac left or cavity,s ot hat groups on all sides of the target may be addressed. Most targets will contain some hydrophobic surface,even if it is small, and this should also be complemented by apolar surfaces in the receptor (Figure 3).…”

Section: General Strategiesmentioning

confidence: 99%

“…Carbohydrates are especially challenging targets when dissolved in water, due to their hydrophilic nature and their general similarity to clusters of solvent. [21] Unlike peptides such as 33 and 35,s accharides mostly lack extended hydrophobic surfaces which can be used to provide the main driving force for binding.H ydrogen bonding is expected to play an important role,b ut placing enough polar groups in the right positions is difficult. Even natural carbohydrate binding tends to be weak, and synthetic carbohydrate receptors have mostly shown very low affinities.T he authors group have pursued the binding of the "all-equatorial" family of carbohydrates, including glucose 37,e mploying designs which sandwich the substrates between aromatic surfaces,complementary to axial CH groups,and H-bond to substrate OH using polar spacers.…”

Section: Carbohydratesmentioning

confidence: 99%

“…Carbohydrates are especially challenging targets when dissolved in water, due to their hydrophilic nature and their general similarity to clusters of solvent [21] . Unlike peptides such as 33 and 35 , saccharides mostly lack extended hydrophobic surfaces which can be used to provide the main driving force for binding.…”

Section: Host–guest Binding By Amphiphilic Receptors In Watermentioning

confidence: 99%

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Molecular Recognition Mediated by Hydrogen Bonding in Aqueous Media

Dong

Davis

2020

Angewandte Chemie

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Hydrogen bonding is a key governing force in molecular recognition, notably in biological systems. While it has been studied and exploited by supramolecular chemists for many years, most of this work has been conducted in organic solvents. Investigations in water, the biological solvent, have proceeded more slowly, largely because the interaction is weakened by solvation and less easy to detect. Recently it has become appreciated that the problems should be addressed, and work towards the deployment of H‐bonding in water has accelerated. This Minireview discusses a range of synthetic receptors designed to bind organic molecules in aqueous media by combining hydrogen bonding with hydrophobic interactions. Some of these systems are capable of high affinities and selectivities, raising the hope of biomedical applications in the near future.

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Section: Design and Synthesis Of Receptors For Studies In Watermentioning

confidence: 93%

Section: General Strategiesmentioning

confidence: 99%

Section: Carbohydratesmentioning

confidence: 99%

Section: Host–guest Binding By Amphiphilic Receptors In Watermentioning

confidence: 99%

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Molecular Recognition Mediated by Hydrogen Bonding in Aqueous Media

Dong

Davis

2020

Angewandte Chemie

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“…[5] Metal-organic cages in particular have found wide uses, due to their versatile and tunable host-guest chemistry, straightforward synthetic accessibility, structural adaptability and stimuli-responsive transformations. [4b, 6] Hydrogen-bonding is widely used for molecular recognition and self-assembly, such as the formation of gels using a series of rigid bis(urea) building blocks, [7] the construction of anion-coordination-based tetrahedral cages and triple helices, [8] the generation of a hydrogen-bonded octameric nano-spheroid, [9] a cryptand-like cage that uses only C À H•••X À hydrogen bonding to trap chloride with exceptional affinity, [10] and covalent organic cages for monosaccharide [11] or anion [12] binding.…”

mentioning

confidence: 99%

Glucose Binding Drives Reconfiguration of a Dynamic Library of Urea‐Containing Metal–Organic Assemblies

Yang

Krbek

et al. 2021

Angew Chem Int Ed

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A bis‐urea‐functionalized ditopic subcomponent assembled with 2‐formylpyridine and FeII, resulting in a dynamic library of metal–organic assemblies: an irregular FeII4L6 structure and three FeII2L3 stereoisomers: left‐ and right‐handed helicates and a meso‐structure. This library reconfigured in response to the addition of monosaccharide derivatives, which served as guests for specific library members, and the rate of saccharide mutarotation was also enhanced by the library. The (P) enantiomer of the FeII2L3 helical structure bound β‐D‐glucose selectively over α‐D‐glucose. As a consequence, the library collapsed into the (P)‐FeII2L3 helicate following glucose addition. The α‐D‐glucose was likewise transformed into the β‐D‐anomer during equilibration and binding. Thus, β‐D‐glucose and (P)‐3 amplified each other in the product mixture, as metal–organic and saccharide libraries geared together into a single equilibrating system.

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Biomimetic Glucose Trigger‐Insulin Release System Based on Hydrogel Loading Bidentate β‐Cyclodextrin

Wang

Tian

Wang

et al. 2021

Adv Funct Materials

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Initiated by the specific binding between D-glucose and biological receptors, the human body has a delicate metabolic system to regulate blood D-glucose levels, but failing to release insulin would induce hyperglycemia or type I diabetes. While insulin delivery is an effective form of hyperglycemia therapy, the self-regulated triggering of insulin release for on-demand supplementation remains inadequate. Here, a biomimetic glucose trigger-insulin release system, that is, a bidentate β-cyclodextrin-based hydrogel with preloaded insulin is presented; the dual self-regulated system shows a specific D-glucose response to realize accurate monitoring and simultaneous on-demand trigger insulin release. The specific binding between D-glucose and the bidentate β-cyclodextrin induces the release of protons, causing macroscopic swelling of the hydrogel, subsequently triggering the on-demand and long-term supplementation of insulin. On the contrary, isomers of D-glucose, such as D-fructose and D-galactose, cause shrinking of the hydrogel, and retard insulin release. In-vivo studies in type I diabetic mice model ascertain that although the bidentate β-CD hydrogel is preloaded with short-activity insulin, it exerts long-activity control of blood glucose level over 12 h.

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Biomimetic carbohydrate recognition

Abstract: Binding saccharides with non-covalent interactions is challenging, especially in the natural medium of water, but synthetic carbohydrate receptors can be surprisingly effective.

Cited by 117 publications

References 55 publications

Molecular Recognition Mediated by Hydrogen Bonding in Aqueous Media

Molecular Recognition Mediated by Hydrogen Bonding in Aqueous Media

Glucose Binding Drives Reconfiguration of a Dynamic Library of Urea‐Containing Metal–Organic Assemblies

Biomimetic Glucose Trigger‐Insulin Release System Based on Hydrogel Loading Bidentate β‐Cyclodextrin

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