Diastereomeric Recognition of Chiral Foldamer Receptors for Chiral Glucoses

Li, Chuang; Wang, Gui-Tao; Yi, Hui‐Ping; Jiang, Xiumin; Li, and Zhan-Ting; Wang, Renxiao

doi:10.1021/ol070492l

Cited by 124 publications

(60 citation statements)

References 23 publications

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“…Moreover, carbohydrate recognition in organic media can be biomimetic in the sense of mimicking recognition at the membrane-cytosol interface, especially if extraction from water can be demonstrated. Accordingly, there has been considerable work in this area over the past 20 years, as recorded in a number of reviews [24,36,48,49] and recent articles [50][51][52][53][54][55][56][57][58][59]. For reasons of space, we will not attempt a further discussion of this work but will proceed to our major topic of carbohydrate recognition in water.…”

Section: Synthetic Lectin Design Principlesmentioning

confidence: 99%

Progress in biomimetic carbohydrate recognition

Walker

Joshi

Davis

2009

Cell. Mol. Life Sci.

109

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The importance of carbohydrate recognition in biology, and the unusual challenges involved, have lead to great interest in mimicking saccharide-binding proteins such as lectins. In this review, we discuss the design of artificial carbohydrate receptors, focusing on those which work under natural (i.e. aqueous) conditions. The problem is intrinsically difficult because of the similarity between substrate (carbohydrate) and solvent (water) and, accordingly, progress has been slow. However, recent developments suggest that solutions can be found. In particular, the "temple" family of carbohydrate receptors show good affinities and excellent selectivities for certain all-equatorial substrates. One example is selective for O-linked beta-N-acetylglucosamine (GlcNAc, as in the O-GlcNAc protein modification), while another is specific for beta-cellobiosyl and closely related disaccharides. Both show roughly millimolar affinities, matching the strength of some lectin-carbohydrate interactions.

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Section: Synthetic Lectin Design Principlesmentioning

confidence: 99%

Progress in biomimetic carbohydrate recognition

Walker

Joshi

Davis

2009

Cell. Mol. Life Sci.

109

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“…However, studies on the recognition behavior of linear receptors were reported in 1970s, while Vögtle et al reported the complexing properties of oligo(ethylene glycol) derivatives toward metal ions [6] . More recently, the present authors and Huc et al found that rationally designed hydrogen bonded aromatic amide or hydrazide-based foldamers could bind neutral or ionic guests in more selective manner [7][8][9][10][11][12][13][14][15] , which mainly depends on the size of their cavity, through multiple intermolecular hydrogen bonds. For all the reported oligomers, the presence of a successive network of intramolecular hydrogen bonds forces the backbones to adopt well-predicted folded or helical conformations, which significantly reduces the binding-initiated negative entropy.…”

Section: Introductionmentioning

confidence: 64%

“…We previously reported a class of aromatic hydrazidebased foldamers forced by successive intramolecular hydrogen bonds to form helical conformation [7,11,12] , in which half of the C== O groups are located inward and thus efficiently bind alkylated saccharides via multiple intermolecular hydrogen bonds in chloroform. It was envisioned that the decrease of the intramolecular hydrogen bonds would increase the conformational flexibility, which might lead to the reduction of the binding capacity.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Complexation of two non-fully hydrogen bonded aromatic hydrazide heptamers toward n-octyl-α-L-glucopyranoside in chloroform

Jiang

et al. 2008

Sci. China Ser. B-Chem.

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Two aromatic hydrazide haptamers have been prepared, with both consisting of two hydrogen bonded folded segments. Compared to their fully hydrogen bonded analogues, the flexibility of their backbones increases due to lack of one or two intramolecular hydrogen bonds at the middle aromatic unit. (2D) 1 H NMR, circular dichroism and fluorescent studies revealed that both oligomers moderately complex n-octyl-α-L-glucopyranoside in chloroform. molecular recognition, hydrogen bonding, foldamer, hydrazide, saccharide

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“…When two chiral proline groups were appended to the ends of the backbone, the resulting foldamers 17a-c produced helicity bias, which was evidenced by circular dichroism experiments. [35] In order to investigate the stacking of this class of folded backbones, foldamers 18a and 18b were also prepared. [36] The introduction of the amphiphilic amide side chains provided the oligomers with solubility in polar organic solvents, in which the folded backbone stacked strongly to generate vesicles or organogels, depending on the solvents used.…”

Section: Aromatic Urea and Hydrazide Backbonesmentioning

confidence: 99%

Hydrogen‐Bonding‐Driven Aromatic Foldamers: Their Structural and Functional Evolution

Zhang

Wang

2014

The Chemical Record

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This Personal Account summarizes the development of the design of hydrogen-bonding-driven aromatic foldamers and their applications in supramolecular chemistry. This account begins with a short, non-exhaustive description of the background in the study of hydrogen-bonded aromatic foldamers. The construction of foldamers from discrete aromatic residues, including amide, urea, hydrazide and 1,2,3-triazole units, is then described. In the following parts, the applications of such compact aromatic oligomers in supramolecular chemistry, including the development of acyclic receptors, the construction of hybrid helical sequences through intramolecular stacking, the promotion of the formation of covalently and noncovalently bonded macrocycles, the tuning of the mechanical properties of copolymers, and the regulation of the shuttling behavior of [2]rotaxanes and the controlled release of dye from reverse vesicles formed from them, are described. In the final part, the binding-induced folding of conformationally flexible aromatic amide oligomers and their self-binding are described.

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Diastereomeric Recognition of Chiral Foldamer Receptors for Chiral Glucoses

Cited by 124 publications

References 23 publications

Progress in biomimetic carbohydrate recognition

Progress in biomimetic carbohydrate recognition

Complexation of two non-fully hydrogen bonded aromatic hydrazide heptamers toward n-octyl-α-L-glucopyranoside in chloroform

Hydrogen‐Bonding‐Driven Aromatic Foldamers: Their Structural and Functional Evolution

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