Selective Recognition of <scp>d</scp>-Aldohexoses in Water by Boronic Acid-Functionalized, Molecularly Imprinted Cross-Linked Micelles

Awino, Joseph K.; Gunasekara, Roshan W.; Zhao, Yan

doi:10.1021/jacs.6b04613

Cited by 79 publications

(65 citation statements)

References 44 publications

(95 reference statements)

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“…16 The selectivity suggests that the C2 and C4 hydroxyls were critical to the molecular recognition and any inversion at these positions shuts off the binding. The C6 hydroxyl was also essential, as xylose, lacking this hydroxyl, showed no binding.…”

Section: Resultsmentioning

confidence: 99%

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A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water

2017

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Molecular recognition of carbohydrates plays vital roles in biology but has been difficult to achieve with synthetic receptors. Through covalent imprinting of carbohydrates in boroxole-functionalized cross-linked micelles, we prepared nanoparticle receptors for a wide variety of mono- and oligosaccharides. The boroxole functional monomer bound the sugar templates through cis-1,2-diol, cis-3,4-diol, and trans-4,6-diol. The protein-sized nanoparticles showed excellent selectivity for D-aldohexoses in water with submillimolar binding affinities and completely distinguished the three biologically important hexoses (glucose, mannose, and galactose). Glycosides with nonpolar aglycon showed stronger binding due to enhanced hydrophobic interactions. Oligosaccharides were distinguished based on their monosaccharide building blocks, glycosidic linkages, chain length, as well as additional functional groups that could interact with the nanoparticles.

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Section: Resultsmentioning

confidence: 99%

“…16 The MINP receptors could distinguish D-aldohexoses with remarkable selectivity. For example, MINP(glucose), i.e., MINP prepared with glucose as the template, bound glucose with K a = 1.18 × 10 3 M −1 .…”

Section: Introductionmentioning

confidence: 99%

A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water

2017

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“…Although the micelles are highly cross-linked, because polymerization and cross-linking are confined within the micellar boundary, MINPs are fully soluble in water due to their hydrophobic/hydrophilic core–shell morphology and nanodimension (4–5 nm). Using this technique, we have created strong and selective receptors for a number of different guests including bile salt derivatives, 30 aromatic carboxylates and sulfonates, 31–33 nonsteroidal anti-inflammatory drugs (NSAIDs), 34 carbohydrates, 35, 36 and oligopeptides. 37 …”

Section: Introductionmentioning

confidence: 99%

Imprinted micelles for chiral recognition in water: shape, depth, and number of recognition sites

Awino

Zhao

2017

Org. Biomol. Chem.

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Chiral molecular recognition is important to biology, separation, and asymmetric catalysis. Because there is no direct correlation between the chiralities of the host and the guest, it is difficult to design a molecular receptor for a chiral guest in a rational manner. By cross-linking surfactant micelles containing chiral template molecules, we obtained chiral nanoparticle receptors for a number of 4-hydroxyproline derivatives. Molecular imprinting allowed us to transfer the chiral information directly from the guest to host, making the molecular recognition between the two highly predictable. Hydrophobic interactions between the host and the guest contributed strongly to the enantio- and diastereoselective differentiation of these compounds in water, whereas ion-pair interactions, which happened near the surface of the micelle, were less discriminating. The chiral recognition could be modulated by turning the size and shape of the binding pockets.

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“…Zhao et al developed the biologically signicant sensor for glucose, mannose, and galactose through the borate affinity MIP method, 145 as depicted in Fig. 15.…”

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confidence: 99%

Recent development of boronic acid-based fluorescent sensors

et al. 2018

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As Lewis acids, boronic acids can bind with 1,2-or 1,3-diols in aqueous solution reversibly and covalently to form five or six cyclic esters, thus resulting in significant fluorescence changes. Based on this phenomenon, boronic acid compounds have been well developed as sensors to recognize carbohydrates or other substances. Several reviews in this area have been reported before, however, novel boronic acid-based fluorescent sensors have emerged in large numbers in recent years. This paper reviews new boronbased sensors from the last five years that can detect carbohydrates such as glucose, ribose and sialyl Lewis A/X, and other substances including catecholamines, reactive oxygen species, and ionic compounds. And emerging electrochemically related fluorescent sensors and functionalized boronic acid as new materials including nanoparticles, smart polymer gels, and quantum dots were also involved.By summarizing and discussing these newly developed sensors, we expect new inspiration in the design of boronic acid-based fluorescent sensors.

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Selective Recognition of d-Aldohexoses in Water by Boronic Acid-Functionalized, Molecularly Imprinted Cross-Linked Micelles

Cited by 79 publications

References 44 publications

A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water

A General Method for Selective Recognition of Monosaccharides and Oligosaccharides in Water

Imprinted micelles for chiral recognition in water: shape, depth, and number of recognition sites

Recent development of boronic acid-based fluorescent sensors

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