Stereoselective Interaction between DNA and Stable Chiral Surfaces Modified with 1,2‐Diphenylethylenediamine Enantiomers

Wang, Lilan; Fu, Yingzi; Zhou, Juan; Qiao, Chunming

doi:10.1002/elan.201000476

Cited by 9 publications

(6 citation statements)

References 34 publications

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“…CV analysis has been widely applied for the chiral recognition of electroactive isomers. , Here, we first investigated the enantioselectivity of nonelectroactive isomers by using this strategy. Taking Thr isomers as an example, experimental parameters, including the pH, metal ion content, concentration, and temperature, were discussed in detail.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Limiting Transport into a Fixed Cavity via Supramolecular Interaction for the Chiral Electroanalysis of Amino Acids Regardless of Electroactive Units

Pan

Gao

et al. 2020

Anal. Chem.

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Although an increasing number of researchers are developing electroanalytical protocols for the chiral recognition of amino acids, the electroactive units of the tested isomers still need to provide corresponding electrical signals. In this study, a supramolecular system was developed for the chiral electroanalysis of amino acids regardless of electroactive units. As a model system, an enantiopure electroactive molecule Fc-(S,S)-1 that includes a ferrocenyl group was synthesized and acted as a guest. Moreover, hydrophobic cyclobis-(paraquat-p-phenylene) (CBPQT 4+ -2) was used as the host. In the presence of π−π stacking and the attraction of π-electrons, CBPQT 4+ -2 can encapsulate Fc-(S,S)-1 into its cavity. Next, a screen-printed electrode was utilized for electrochemical chiral recognition. The host was fixed on the surface of the working electrode, and the guest was used as the electroactive chiral selector to support electron transfer. Once different configurations of amino acids (threonine, histidine, glutamine, and leucine) were mixed with the guest, regardless of whether they contained electroactive units, differences in the cyclic voltammetry results of the probe enantiomers could be observed, namely, in the peak currents or peak potentials. However, glutamine was an exception because the L-isomer had a stronger binding affinity with Fc-(S,S)-1 + Cu(II), which would limit the transport of the complex into the cavity of CBPQT 4+ -2, thereby resulting in a low peak current. Thus, an inverse phenomenon was observed with glutamine. In summary, we believe that this work can increase the testing scope for the chiral recognition of different kinds of isomers using electrochemical tools.

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Section: Resultsmentioning

confidence: 99%

Enantioselective Limiting Transport into a Fixed Cavity via Supramolecular Interaction for the Chiral Electroanalysis of Amino Acids Regardless of Electroactive Units

Pan

Gao

et al. 2020

Anal. Chem.

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“…The AFM image of the bare gold substrate was smooth and uniform. 38 When Van was modied to the surface, increased roughness and a particle-like morphology were both apparent in the image (Fig. 3A).…”

Section: Afm Characterization Of the Pen Enantiomers On Van-surfacementioning

confidence: 98%

“…Enantiomers present different morphologies when they are in chiral environments. 11,38 AFM was employed to observe the surface morphologies of the Van-surface and the Pen enantiomers on the Van-surface. The AFM image of the bare gold substrate was smooth and uniform.…”

Section: Afm Characterization Of the Pen Enantiomers On Van-surfacementioning

confidence: 99%

Chiral recognition of penicillamine enantiomers based on a vancomycin membrane electrode

et al. 2013

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An enantioselective membrane electrode based on vancomycin (Van) was proposed for the assay of penicillamine enantiomers. Cyclic voltammetry, electrochemical impedance spectroscopy, atomic force microscopy and UV-Vis spectra were employed to investigate the chiral recognition phenomenon. The results exhibited that the binding effect between D-penicillamine (D-Pen) and the proposed Van membrane electrode was obviously stronger than that of L-penicillamine (L-Pen). In addition, the amount of Van, the pH of the supporting electrolyte solution and the concentration of Pen enantiomers were systematically investigated and optimized. The association constant (K) was calculated to be 1.05 Â 10 4 L mol À1 for D-Pen and 1.40 Â 10 2 L mol À1 for L-Pen. The enantioselective concentration range of the proposed membrane electrode is 10 À7 to 10 À2 mol L À1 . The results suggested that the chiral selective membrane has the potential to discriminate and determine chiral drugs in the pharmaceutical application of electrochemical analysis. Fig. 1 The structures of (a) Van and (b) Pen.

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“…scanning tunneling microscopy (STM) 65 and atomic force microscopy (AFM). 66 In different environments, DNA molecules have various conformations with distinct bioactivities, which can be mainly divided into two categories-relaxed and folding structures. The later ones are beneficial for DNA molecules to preserve the stereo-configuration and genetic information from external damages, and in living organisms, DNA molecules mainly exist in highly folded conformations to perform their bio-functions; whereas DNA may exhibit lower activities in gene manipulation for the relaxed forms.…”

Section: Chiral Interface Materials To Improve Anti-biofoulingmentioning

confidence: 99%

Chiral biointerface materials

2012

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Chiral phenomena are ubiquitous in nature from macroscopic to microscopic, including the high chirality preference of small biomolecules, special steric conformations of biomacromolecules induced by it, as well as chirality-triggered biological and physiological processes. The introduction of chirality into the study of interface interactions between materials and biological systems leads to the generation of chiral biointerface materials, which provides a new platform for understanding the chiral phenomena in biological system, as well as the development of novel biomaterials and devices. This critical review gives a brief introduction to the recent advances in this field. We start from the fabrication of chiral biointerface materials, and further investigate the stereo-selective interaction between biological systems and chiral interface materials to find out key factors governing the performance of such materials in given conditions, then introduce some special functionalities and potential applications of chiral biointerface materials, and finally present our own thinking about the future development of this area (108 references).

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Stereoselective Interaction between DNA and Stable Chiral Surfaces Modified with 1,2‐Diphenylethylenediamine Enantiomers

Cited by 9 publications

References 34 publications

Enantioselective Limiting Transport into a Fixed Cavity via Supramolecular Interaction for the Chiral Electroanalysis of Amino Acids Regardless of Electroactive Units

Enantioselective Limiting Transport into a Fixed Cavity via Supramolecular Interaction for the Chiral Electroanalysis of Amino Acids Regardless of Electroactive Units

Chiral recognition of penicillamine enantiomers based on a vancomycin membrane electrode

Chiral biointerface materials

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