Locally superengineered cascade recognition–quantification zones in nanochannels for sensitive enantiomer identification

Guo, Jianhua; Xu, Huijie; Zhao, Jiulong; Gao, Zhida; Wu, Zeng-Qiang; Song, Yan‐Yan

doi:10.1039/d2sc03198a

Cited by 9 publications

(3 citation statements)

References 58 publications

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“…Chromatography and optical methods (e.g., circular dichroism, fluorescence and Raman spectroscopies), as widely used chiral recognition techniques, usually require high‐cost chiral chromatography columns or expensive apparatuses, and sometimes need complex sample pretreatments. [ 28 ] In contrast, nanopore‐based electrochemical methods exhibit advantages of simple sample pretreatment, low‐cost instruments, high sensitivity, and high integratability, [ 29,30 ] showing great potential as a platform for chiral recognition.…”

Section: Introductionmentioning

confidence: 99%

Homochiral Zeolitic Imidazolate Framework with Defined Chiral Microenvironment for Electrochemical Enantioselective Recognition

Ding

et al. 2023

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The recognition and separation of chiral molecules with similar structure are of great industrial and biological importance. Development of highly efficient chiral recognition systems is crucial for the precise application of these chiral molecules. Herein, a homochiral zeolitic imidazolate frameworks (c‐ZIF) functionalized nanochannel device that exhibits an ideal platform for electrochemical enantioselective recognition is reported. Its distinct chiral binding cavity enables more sensitive discrimination of tryptophan (Trp) enantiomer pairs than other smaller chiral amino acids owing to its size matching to the target molecule. It is found that introducing neighboring aldehyde groups into the chiral cavity will result in an inferior chiral Trp recognition due to the decreased adsorption‐energy difference of D‐ and L‐Trp on the chiral sites. This study may provide an alternative strategy for designing efficient chiral recognition devices by utilizing the homochiral reticular materials and tailoring their chiral environments.

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Section: Introductionmentioning

confidence: 99%

Homochiral Zeolitic Imidazolate Framework with Defined Chiral Microenvironment for Electrochemical Enantioselective Recognition

Ding

et al. 2023

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“…Two enantiomers of the same drug can differ in pharmacodynamics and pharmacokinetics; one is useful, while the other might even bring severe side effects. , Hence, discriminating chiral molecules with absolute configurations is essential for life-science applications. Amino acids are predominant in natural chiral compounds, and the l -/ d -enantiomers have different effects on organisms. , Therefore, the discrimination and quantification of amino acid enantiomers are favorable solutions for diagnosing and curing diseases. − Cystine plays a critical role in maintaining cellular redox balance by regulating intracellular glutathione synthesis, selected as a representative enantiomer for amino acids and disulfide-containing chiral drugs. However, few studies have been reported on the discrimination of cystine enantiomers. , High-performance liquid chromatography (HPLC) techniques and Raman spectroscopy are used with several common shortcomings, such as a time-consuming pretreatment process and a high-price instrument.…”

mentioning

confidence: 99%

Target Recognition-Triggered Peroxidase-Mimicking Activity Depression in Homochiral Nanochannels for Identifying Cystine Enantiomers

Guo

Zhao

et al. 2023

Anal. Chem.

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Enantioselective identification of chiral molecules is of paramount importance in medical science, biochemistry, and pharmaceutics owing to the configuration-dependent activities of enantiomers. However, the identical physicochemical properties of enantiomers remain challenging in chiral sensing. In this study, inspired by the peroxidase-mimicking activity of Fe(III)-based nanomaterials, an enantioselective artificial architecture is constructed on TiO2 nanochannels. Homochiral Ti-based metal–organic frameworks (MOFs) use a 2,2′-bipyridine-5,5′-dicarboxylic acid ligand as the artificial enzyme skeleton, Fe(III) as peroxidase-mimicking centers, and l-tartaric acid (TA) as a chiral recognition selector. Using l-/d-cystine as model enantiomers, the chiral moieties of l-TA on Ti-MOFs allow stereoselective recognition of guest molecules through hydrogen bonds formed between chiral cystine and the host. In a tris(2-carboxyethyl)phosphine hydrochloride-containing environment, the disulfide bonds in cystine molecules are further cleaved, and the HS-tails react with Fe(III) active sites, causing the loss of peroxidase-like performance of nanochannels. Benefitting from the nanochannel architecture’s current–potential (I–V) properties, the selective recognition of cystine enantiomers is directly monitored through the peroxidase-like activity change-induced ionic current signatures. This study provides a new and universal strategy for distinguishing disulfide- and thiol-containing chiral molecules.

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“…Numerous advancements in chiral recognition have been made through a variety of techniques in an effort to increase the understanding and application of chirality. In addition to chiral chromatography, other techniques, such as nuclear magnetic resonance (NMR) spectroscopy, capillary electrophoresis, circular dichroism (CD) spectroscopy, fluorescence spectroscopy, colorimetry, surface-enhanced Raman scattering spectroscopy, electrochemical assay, − fiber probe, and photoelectrochemical sensors, have been developed for selective chiral detection, which has been extensively studied over the past decade. However, the above-mentioned techniques typically require expensive equipment, reagents, and external energy, which severely limits their applicability as point-of-care devices used outside the laboratory.…”

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confidence: 99%

Water Evaporation-Driven Arginine Enantiomer Recognition on a Self-Powered Flexible Chip with High Specificity

Zhang

Guo

et al. 2023

Anal. Chem.

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Chiral recognition is a crucial issue in the biomedical and pharmaceutical research communities. Due to the need for expensive equipment, reagents, and external energy, enantiomer identification is difficult to perform outside of a laboratory. Based on water evaporation-induced hydrovoltaic effect, a power-free sensing platform with sensitive chiral recognition capability is proposed for the discrimination of enantiomers. The chiral recognizer was bovine serum albumin (BSA), a naturally occurring protein. Using arginine (Arg) enantiomers as the sensing targets, the difference in enantioselectivity between l-Arg and d-Arg on a BSA-modified porous carbon substrate can be measured directly from the output voltage. By combining the cyclization reaction between NO and O-phenylenediamine (OPD), it has been discovered that the sensitivity and specificity of enantioselective identification can be significantly enhanced based on the surface charges. The limit of detection (LOD) could be as low as 76.0 nM. In addition, the proposed chips are extremely flexible and can function under deformation without sacrificing output performance. This self-powered chiral recognition chip paves a new path for the detection of chiral molecules at any time, any place, and it also has excellent potential for use in flexible wearable technology.

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Locally superengineered cascade recognition–quantification zones in nanochannels for sensitive enantiomer identification

Abstract: As an intriguing and intrinsic feature of life, chirality is highly associated with many significant biological processes. Simultaneous recognition and quantification of enantiomers remains a major challenge. Here, a sensitive...

Cited by 9 publications

References 58 publications

Homochiral Zeolitic Imidazolate Framework with Defined Chiral Microenvironment for Electrochemical Enantioselective Recognition

Homochiral Zeolitic Imidazolate Framework with Defined Chiral Microenvironment for Electrochemical Enantioselective Recognition

Target Recognition-Triggered Peroxidase-Mimicking Activity Depression in Homochiral Nanochannels for Identifying Cystine Enantiomers

Water Evaporation-Driven Arginine Enantiomer Recognition on a Self-Powered Flexible Chip with High Specificity

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