Glycoluril derivatives as precursors in the preparation of substituted cucurbit[n]urils

Jansen, K.; Wego, Andreas; Buschmann, Hans‐Jürgen; Schollmeyer, Eckhard; Döpp, D.

doi:10.1163/156855503321127529

Cited by 27 publications

(14 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Ideally, if the CB[n] family could be modified to improve their solubility and to provide different functional groups that allow further derivatization, the range of potential applications would be significantly expanded. [68][69][70][71][72][73][74][75][76][77][78] In a major breakthrough in the CB chemistry, we discovered a direct functionalization method to produce perhydroxylated products of CB[n] through oxidation with K 2 S 2 O 8 in water. 28 The functionalization was achieved either by use of substituted glycoluril derivatives in CB[n]-forming reactions or by direct substitution at the ''equator'' positions of CB[n].…”

Section: Applications Of High-affinity Cb[7] Complexesmentioning

confidence: 99%

Can we beat the biotin–avidin pair?: cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications

et al. 2015

View full text Add to dashboard Cite

The design of synthetic, monovalent host-guest molecular recognition pairs is still challenging and of particular interest to inquire into the limits of the affinity that can be achieved with designed systems. In this regard, cucurbit[7]uril (CB[7]), an important member of the host family cucurbit[n]uril (CB[n], n = 5-8, 10, 14), has attracted much attention because of its ability to form ultra-stable complexes with multiple guests. The strong hydrophobic effect between the host cavity and guests, ion-dipole and dipole-dipole interactions of guests with CB portals helps in cooperative and multiple noncovalent interactions that are essential for realizing such strong complexations. These highly selective, strong yet dynamic interactions can be exploited in many applications including affinity chromatography, biomolecule immobilization, protein isolation, biological catalysis, and sensor technologies. In this review, we summarize the progress in the development of high affinity guests for CB[7], factors affecting the stability of complexes, theoretical insights, and the utility of these high affinity pairs in different challenging applications.

show abstract

Section: Applications Of High-affinity Cb[7] Complexesmentioning

confidence: 99%

Can we beat the biotin–avidin pair?: cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications

et al. 2015

View full text Add to dashboard Cite

show abstract

“…T. decomp. more 270°C ( [ 49 ] : 254°C). 1 H NMR (400 MHz, D 2 O): δ = 4.43 (s. 1Н, СН), 1.45 (s. 3Н, СН 3 ).…”

Section: Resultsunclassified

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2‐dicarbonyl compounds using etidronic acid as a “green catalyst”

Бакибаев

Uhov

Malkov

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as "Green catalyst." So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80 C-90 C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.

show abstract

“…Synthesis of clip 1 was illustrated in Scheme . Dimethyl glycoluril ( 2 ) and dimethyl glycoluril‐bis(ether) ( 3 ) were synthesized according to a known procedure . The clip 1 was synthesized by 3 fused with 2,7‐dihydroxynaphthalene.…”

Section: Resultsmentioning

confidence: 99%

A New Fluorescent Sensor for Fe³⁺ Based on Glycoluril Molecular Clip

et al. 2020

View full text Add to dashboard Cite

The application of fluorescent method to metal ions detection features high sensitivity, simple operation and real‐time monitoring. A 2,7‐dihydroxynaphthalene‐functionalized dimethyl glycoluril (called clip 1) was synthesized, using a relatively simple method. And it is fully characterized by 1H NMR, 13C NMR, HR‐MS and single crystal X‐ray diffraction. The recognition properties of molecular clip 1 were analyzed systematically toward several metal ions using fluorescence spectroscopy, and it was found that molecular clip 1 is selective and sensitive to Fe3+. At the same time, the clip 1 shows good anti‐interference ability when other metal ions existed. The limit detection of Fe3+ is 3×10−7M. The fluorescence of clip 1 was quenched apparently by Fe3+, which was speculated to be caused by ligand–metal charge transfer mechanism (LMCT). As a new fluorescence probe for Fe3+ ion, it may expanded the application of glycoluril molecular clips.

show abstract

Glycoluril derivatives as precursors in the preparation of substituted cucurbit[n]urils

Cited by 27 publications

References 25 publications

Can we beat the biotin–avidin pair?: cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications

Can we beat the biotin–avidin pair?: cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2‐dicarbonyl compounds using etidronic acid as a “green catalyst”

A New Fluorescent Sensor for Fe³⁺ Based on Glycoluril Molecular Clip

Contact Info

Product

Resources

About

Glycoluril derivatives as precursors in the preparation of substituted cucurbit[n]urils

Cited by 27 publications

References 25 publications

Can we beat the biotin–avidin pair?: cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications

Can we beat the biotin–avidin pair?: cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2‐dicarbonyl compounds using etidronic acid as a “green catalyst”

A New Fluorescent Sensor for Fe3+ Based on Glycoluril Molecular Clip

Contact Info

Product

Resources

About

A New Fluorescent Sensor for Fe³⁺ Based on Glycoluril Molecular Clip