859 results match your criteria enantioselective recognition


Artificial Biomolecular Channels: Enantioselective Transmembrane Transport of Amino Acids Mediated by Homochiral Zirconium Metal-Organic Cages.

J Am Chem Soc 2021 Dec 1. Epub 2021 Dec 1.

School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China.

Natural transport channels (or carriers), such as aquaporins, are a distinct type of biomacromolecule capable of highly effective transmembrane transport of water or ions. Such behavior is routine for biology but has proved difficult to achieve in synthetic systems. Perhaps most significantly, the enantioselective transmembrane transport of biomolecules is an especially challenging problem both for chemists and for natural systems. Read More

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December 2021

Enantioselective recognition of chiral acids by supramolecular interactions with chiral AIEgens.

Chem Commun (Camb) 2021 Nov 23. Epub 2021 Nov 23.

Shenzhen Institute of Aggregate Science and Technology, School of Science and Engineering, The Chinese University of Hong Kong, Shenzhen, Guangdong 518172, China.

Novel chiral AIEgens bearing optically pure amino groups were synthesized and showed excellent discrimination for a series of chiral acidic compounds and amino acids. Interestingly, after supramolecular assembly with 4-sulfocalix[4]arene, the obtained complexes showed enhanced enantioselectivity for chiral acids. Read More

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November 2021

Plasmonic Nanosensors with Extraordinary Sensitivity to Molecularly Enantioselective Recognition at Nanoscale Interfaces.

ACS Nano 2021 Nov 19. Epub 2021 Nov 19.

School of Physics, Beijing Institute of Technology, Beijing 100081, China.

Molecular chirality recognition plays a pivotal role in chiral generation and transfer in living systems and makes important contribution to the development of diverse applications spanning from chiral separation to soft nanorobots. To detect chirality recognition, most of the molecular sensors described to date are based on the design and preparation of the host-guest complexation with chromophore or fluorophore at the reporter unit. Nevertheless, the involved tedious procedures and complicated chemical syntheses hamper their practical applications. Read More

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November 2021

Inducing enantioselective crystallization with and self-assembly of star-shaped hybrid polymers prepared via "grafting to" strategy.

Chirality 2021 Nov 8. Epub 2021 Nov 8.

Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, Anhui Key Laboratory of Advanced Catalytic Materials and Reaction Engineering, Hefei University of Technology, Hefei, Anhui Province, China.

Helical polymers present some interesting and distinctive properties, and one of the most distinguished applications of them is the chiral recognition and resolution of enantiomers. In this work, star-shaped hybrid helical poly (phenyl isocyanide) (PPI) with polyhedral oligomeric silsesquioxanes (POSS) as the core was designed and synthesized by "grafting to" strategy. The homoarm star-shaped hybrid POSS-(PPI) was first obtained by the click reaction between azide-modified POSS (POSS-(N ) ) and alkynyl-modified PPI (PPI-Alkynyl). Read More

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November 2021

Cp*Co(III)-Catalyzed Enantioselective Hydroarylation of Unactivated Terminal Alkenes via C-H Activation.

J Am Chem Soc 2021 Nov 8;143(45):19112-19120. Epub 2021 Nov 8.

Department of Chemistry, Zhejiang University, Hangzhou 310027, China.

Enantioselective hydroarylation of unactivated terminal akenes constitutes a prominent challenge in organic chemistry. Herein, we reported a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by a new type of tailor-made amino acid ligands. Critical to the chiral induction was the engaging of a novel noncovalent interaction (NCI), which has seldomly been disclosed in the C-H activation area, arising from the molecular recognition among the organocobalt(III) intermediate, the coordinated alkene, and the well-designed chiral ligand. Read More

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November 2021

Chirally modified cobalt-vanadate grafted on battery waste derived layered reduced graphene oxide for enantioselective photooxidation of 2-naphthol: Asymmetric induction through non-covalent interaction.

J Colloid Interface Sci 2021 Oct 23;608(Pt 2):1526-1542. Epub 2021 Oct 23.

Department of Chemical Sciences, Tezpur University, Assam 784028, India. Electronic address:

The cobalt oxide-vanadium oxide (CoO-VO) combined with reduced graphene oxide (rGO) having band gap of ∼ 3.3 eV appeared as a suitable photocatalyst for selective oxidation of 2-naphthol to BINOL. C2-symmetric BINOL was achieved with good yield using hydrogen peroxide as the oxidant under UV-light irradiation. Read More

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October 2021

Catalytic Asymmetric Inverse-Electron-Demand Diels-Alder Reactions of 2-Pyrones with Indenes: Total Syntheses of Cephanolides A and B.

Angew Chem Int Ed Engl 2021 Oct 20. Epub 2021 Oct 20.

Department of Chemistry and Research Center for Molecular Recognition and Synthesis, Fudan University, 220 Handan Rd., Shanghai, 200433, China.

An inverse-electron-demand Diels-Alder (IEDDA) reaction could complement the conventional normal-electron-demand Diels-Alder reaction in the synthesis of six-membered carbocycles. However, catalytic asymmetric all-carbon-based IEDDA reactions are underdeveloped. Herein, we disclosed a copper-catalyzed asymmetric IEDDA reaction using electron-deficient 3-carboalkoxyl-2-pyrones and electronically unbiased indenes as reactants. Read More

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October 2021

Unlocking the Stereoselectivity and Substrate Acceptance of Enzymes: Proline-Induced Loop Engineering Test.

Angew Chem Int Ed Engl 2021 Oct 17. Epub 2021 Oct 17.

Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin, 300308, China.

Protein stability and evolvability influence each other. Although protein dynamics play essential roles in various catalytically important properties, their high flexibility and diversity makes it difficult to incorporate such properties into rational engineering. Therefore, how to unlock the potential evolvability in a user-friendly rational design process remains a challenge. Read More

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October 2021

Enantioselective Synthesis of C-Tetrasubstituted -Hydroxyl-α-amino Nitriles via Cyanation of Ketonitrones Using Me(CHCl)SiCN.

Org Lett 2021 Nov 13;23(21):8471-8476. Epub 2021 Oct 13.

Shanghai Key Laboratory of Green Chemistry and Chemical Process and Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062, China.

Here, we report an unprecedented catalytic enantioselective cyanation of ketonitrones enabled by the bifunctional cyanating reagent Me(CHCl)SiCN. This approach allows facile access to optically active -hydroxyl-α-amino nitriles that are of high synthetic value but difficult to acquire by other methods. The use of bifunctional cyanating reagent Me(CHCl)SiCN not only achieves an enantioselectivity higher than that with TMSCN but also enables various diversification reactions of the resulting silylated adducts. Read More

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November 2021

Enantioselective Separation of Chiral N1-Substituted-1-pyrazoles: Greenness Profile Assessment and Chiral Recognition Analysis.

ACS Omega 2021 Oct 23;6(39):25835-25841. Epub 2021 Sep 23.

Department of Analytical Chemistry, Faculty of Pharmacy, University of Sadat City, Sadat City 32897, Egypt.

Two commercialized polysaccharide-based chiral stationary phases, Lux cellulose-2 and Lux amylose-2, were examined for their chiral recognition ability on a set of 18 biologically active racemic 4,5-dihydro-1-pyrazole derivatives by applying normal and polar organic elution modes. The results showed that all compounds were baseline-resolved with at least one of the used elution modes. The cellulose-based column was superior using polar organic mobile-phase compositions with analysis times close to 5 min and resolutions up to 18, while the enantiomer-resolving ability of amylose-based columns was greater using the normal elution mode with analysis times close to 30 min and resolutions up to 30. Read More

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October 2021

Artificial Metal-Peptide Assemblies: Bioinspired Assembly of Peptides and Metals through Space and across Length Scales.

J Am Chem Soc 2021 Oct 7;143(42):17316-17336. Epub 2021 Oct 7.

School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China.

The exploration of chiral crystalline porous materials, such as metal-organic complexes (MOCs) or metal-organic frameworks (MOFs), has been one of the most exciting recent developments in materials science owing to their widespread applications in enantiospecific processes. However, achieving specific tight-affinity binding and remarkable enantioselectivity toward important biomolecules is still challenging. Perhaps most critically, the lack of adaptability, compatibility, and processability in these materials severely impedes practical applications in chemical engineering and biological technology. Read More

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October 2021

Hybrid light-emitting devices for the straightforward readout of chiral information.

Chirality 2021 Dec 7;33(12):875-882. Epub 2021 Oct 7.

Univ. Bordeaux, ISM CNRS UMR 5255, Bordeaux INP, Pessac, France.

Bipolar electrochemistry has gained increasing attention in recent years as an attractive transduction concept in analytical chemistry in general and, more specifically, in the frame of chiral recognition. Herein, we use this concept of wireless electrochemistry, based on the combination of the enantioselective oxidation of a chiral probe with the emission of light from a light-emitting diode (LED), as an alternative for an easy and straightforward readout of the presence of chiral molecules in solution. A hybrid polymer-microelectronic device was designed, using an inherently chiral oligomer, that is, oligo-(3,3'-dibenzothiophene) and a polypyrrole strip as the anode and cathode of a miniaturized LED. Read More

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December 2021

Peak-fitting assisted SERS strategy for accurate discrimination of carboxylic acid enantiomers.

Chem Commun (Camb) 2021 Oct 21;57(84):11064-11067. Epub 2021 Oct 21.

School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. China.

A novel peak-fitting assisted SERS (PF-SERS) strategy was developed for the first time to discriminate carboxylic acid enantiomers. The PF-SERS method offered substantial improvement in accuracy, quantitative performance of enantioselective sensing and exceptionally strong enantiomeric recognition ability. Read More

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October 2021

Structural and biochemical studies enlighten the unspecific peroxygenase from Hypoxylon sp. EC38 as an efficient oxidative biocatalyst.

ACS Catal 2021 Sep 2;11(18):11511-11525. Epub 2021 Sep 2.

Department of Biology and Biotechnology, University of Pavia, via Ferrata 9, 27100 Pavia, Italy.

Unspecific peroxygenases (UPO) are glycosylated fungal enzymes that can selectively oxidize C-H bonds. UPOs employ hydrogen peroxide as oxygen donor and reductant. With such an easy-to-handle co-substrate and without the need of a reducing agent, UPOs are emerging as convenient oxidative biocatalysts. Read More

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September 2021

Enantioselective multiple heart cutting online two-dimensional liquid chromatography-mass spectrometry of all proteinogenic amino acids with second dimension chiral separations in one-minute time scales on a chiral tandem column.

Anal Chim Acta 2021 Oct 19;1180:338858. Epub 2021 Jul 19.

Institute of Pharmaceutical Sciences, Pharmaceutical (Bio-)Analysis, University of Tübingen, Auf der Morgenstelle 8, 72076, Tübingen, Germany. Electronic address:

In this work, we present a unique, robust and fully automated analytical platform technology for the enantioselective amino acid analysis using a multiple heart cutting RPLC-enantio/stereoselective HPLC-ESI-QTOF-MS method. This 2D-LC method allows the full enantioselective separation of 20 proteinogenic AAs plus 5 isobaric analogues, namely allo-Threonine (aThr), homoserine (Hse), allo-isoleucine (aIle), tert-Leucine (Tle) and Norleucine (Nle), after pre-column derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC; AccQ). This N-terminal AA-derivatization method introduces on the one hand beneficial chromatographic properties for D RP-LC (stronger retention) and D chiral separation (better chiral recognition), and on the other hand favorable detection properties with its chromophoric, fluorophoric, and easily ionizable quinoline mass tag. Read More

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October 2021

Decorated traditional cellulose with nanoscale chiral metal-organic frameworks for enhanced enantioselective capture.

Chem Commun (Camb) 2021 Oct 7;57(80):10343-10346. Epub 2021 Oct 7.

Center of Advanced Analysis and Gene Sequencing, Key Laboratory of Molecular Sensing and Harmful Substances Detection Technology, Zhengzhou University, Kexue Avenue 100, Zhengzhou, Henan, 450001, P. R. China.

Herein, a rapid approach toward the size/morphology-controlled synthesis of [Cu(L-mal)(bipy)·2HO] (CuLBH) was developed by adjusting the concentrations of 2-methylimidazole (2-MI) and copper ions. The chiral separation efficiency test indicated that the nano-diameter CuLBH exhibited better selective potential towards (±)-1-(1-naphthyl)ethanol (NE) by providing more fully exposed recognition sites. In order to further improve the selectivity for NE enantiomers and avoid the aggregation of MOF nanoparticles, the nanosized CuLBH-decorated carboxylated cellulose (CC) composite CC-CuLBH was designed by controlling the ratio of the solvent and Cu, which exhibited much higher enantioselectivity than those of pristine CC and even nano CuLBH. Read More

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October 2021

Enantioselective Synthesis of Indanes with a Quaternary Stereocenter via Diastereoselective C(sp)-H Functionalization.

Org Lett 2021 10 10;23(19):7359-7363. Epub 2021 Sep 10.

Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. China.

A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C-H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey-Bakshi-Shibata (CBS) reduction of indanone derivatives. The subsequent diastereospecific and regioselective rhodium-catalyzed silylation of the methyl C-H bond led to indane derivatives with quaternary centers. Read More

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October 2021

Pillararenes: fascinating planar chiral macrocyclic arenes.

Chem Commun (Camb) 2021 Sep 9;57(72):9029-9039. Epub 2021 Sep 9.

Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. China.

Chiral macrocycles possess significant value in chiral science and supramolecular chemistry. Pillararenes, as a class of relatively young supramolecular macrocyclic hosts, have been widely used for host-guest recognition and self-assembly. Since the position of substituents on the benzene rings breaks the molecular symmetry (symmetric plane and symmetric center), pillararenes possess planar chirality. Read More

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September 2021

Self-assembly of chiral BINOL cages imine condensation.

Chem Commun (Camb) 2021 Sep 9;57(72):9088-9091. Epub 2021 Sep 9.

College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, China.

Condensation of an ()- or ()-BINOL-derived dialdehyde and tris(2-aminoethyl)amine produced chiral [2+3] imine cages, which were further reduced to furnish more stable chiral amine cages and applied in the enantioselective recognition of (1,2)- and (1,2)-1,2-diaminocyclohexane. Read More

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September 2021

Porous organic cage for enantiomeric fluorescence recognition of amino acid and hydroxy acid.

Luminescence 2021 Dec 24;36(8):2022-2027. Epub 2021 Sep 24.

College of Material and Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu, China.

A new method based on the enantioselective recognition of porous organic cages CC3-R was established for the first time. Porous organic cages are widely used for separation, adsorption and host-guest interaction sensing, but are rarely used for fluorescence sensing. Based on the inherent chiral environment of CC3-R and the inherent fluorescence properties of the organic ligands constituting the cage, when different chiral monomers diffuse into the cage, different effects occur to produce changes in fluorescence. Read More

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December 2021

A chiral metal-organic framework core-shell microspheres composite for high-performance liquid chromatography enantioseparation.

J Sep Sci 2021 Nov 16;44(21):3976-3985. Epub 2021 Sep 16.

Department of Chemistry, Yunnan Normal University, Kunming, P.R. China.

The unique features of uniform and adjustable cavities, abundant chiral active sites, and high enantioselectivity make chiral metal-organic frameworks popular as an emerging candidate for enantioselective separation. However, the wide particle size distribution and irregular shape of as-synthesized metal-organic frameworks result in low column efficiency, undesired chromatographic peak shape, and high column backpressure of such metal-organic frameworks packed columns. Herein, we report the fabrication of chiral core-shell microspheres [Cu (d-Cam) (4,4'-bpy)] @SiO composite for high-performance liquid chromatography enantioseparation to overcome the above-mentioned problems. Read More

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November 2021

Bovine serum albumin-coated titanium dioxide modified electrochemical interface for enantioselective discrimination of D/L-aspartic acid.

Chirality 2021 10 1;33(10):731-744. Epub 2021 Sep 1.

College of Materials Science and Engineering, Huaqiao University, Xiamen, China.

Due to the similar physicochemical properties, the discrimination of chiral isomers faces huge challenges in drug production and biochemical analysis. Herein, the bovine serum albumin-coated titanium dioxide (bovine serum albumin [BSA]/TiO ) was modified as a novel electrochemical interface for efficient, simple, and enantioselective discrimination of aspartic acid enantiomers (D/L-Asp) based on the electrochemical impedance spectroscopy (EIS). Utilizing the structural characteristics of large cavity and high specific surface area, TiO material provided sufficient space for adequate loading of BSA. Read More

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October 2021

Enantioselective synthesis of ammonium cations.

Nature 2021 09 1;597(7874):70-76. Epub 2021 Sep 1.

Department of Chemistry, Durham University, Durham, UK.

Control of molecular chirality is a fundamental challenge in organic synthesis. Whereas methods to construct carbon stereocentres enantioselectively are well established, routes to synthesize enriched heteroatomic stereocentres have garnered less attention. Of those atoms commonly present in organic molecules, nitrogen is the most difficult to control stereochemically. Read More

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September 2021

Tailored Chiral Copper Selenide Nanochannels for Ultrasensitive Enantioselective Recognition and Detection.

Angew Chem Int Ed Engl 2021 11 18;60(47):24997-25004. Epub 2021 Oct 18.

State Key Lab of Food Science and Technology, International Joint Research Laboratory for Biointerface and Biodetection, School of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu, 214122, P. R. China.

We constructed a tailorable membrane channel system consisting of penicillamine molecules intercalated in copper selenide nanoparticles (Cu Se NPs), which exhibited circular dichroism (CD) bands in the near infrared region (CD, 800-1600 nm) with a maximum intensity of 164.5 mdeg at 1440 nm. The chiral ligand hybridized to the surface of achiral Cu Se NPs by breaking the intrinsic symmetry of Cu Se NPs and further large-scale assembly induced strong optical activity. Read More

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November 2021

Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols a sequential reduction/C-H functionalization.

Chem Sci 2021 Aug 5;12(31):10598-10604. Epub 2021 Jul 5.

Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China

We report here a sequential enantioselective reduction/C-H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C-H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. Read More

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Engineering Homochiral MOFs in TiO Nanotubes as Enantioselective Photoelectrochemical Electrode for Chiral Recognition.

Anal Chem 2021 09 25;93(35):12067-12074. Epub 2021 Aug 25.

College of Sciences, Northeastern University, Shenyang 110004, China.

Enantioselective sensing of chiral molecules is an important issue for both biomedical research and the pharmaceutical industry. Here, an enantioselective photoelectrochemical (PEC) sensor was constructed by integrating TiO nanotubes (NTs) with metal-organic frameworks (MOFs) for the identification of enantiomers. TiO NTs prepared by electrochemical anodization can not only be used as the PEC platform but also as the metal-ion precursor to react with terephthalic acid (BDC) to form MIL-125(Ti) . Read More

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September 2021

Steering Triplet-Triplet Annihilation Upconversion through Enantioselective Self-Assembly in a Supramolecular Gel.

J Am Chem Soc 2021 Aug 13;143(33):13259-13265. Epub 2021 Aug 13.

CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, National Center for Nanoscience and Technology (NCNST), No. 11 ZhongGuanCun BeiYiTiao, 100190 Beijing, People's Republic of China.

Research on chiral selection and recognition not only is of fundamental importance in resolving the origin of biological homochirality, but also is instructive in the fabrication of controlled molecular organization in supramolecular systems to modulate their chirality-related functional properties. Here we report an enantioselective assembly process between a chiral energy donor and two enantiomeric energy acceptors, which further results in chirality-controlled energy transfer and enantioselective triplet-triplet annihilation upconversion (TTA-UC). It is found that the chiral energy donor Pd(II) octaethylporphyrin derivative PdOEP-LG12 () can selectively coassemble with the chiral energy acceptor LGAn () with the same chiral scaffold but tends to form segregation with the energy acceptor DGAn () with the opposite chiral scaffold in a thermodynamic equilibrium state. Read More

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Nitrogen-Doped Chiral CuO/CoO Nanofibers: An Enhanced Electrochemiluminescence Sensing Strategy for Detection of 3,4-Dihydroxy-Phenylalanine Enantiomers.

Anal Chem 2021 08 11;93(33):11470-11478. Epub 2021 Aug 11.

State Key Laboratory of Applied Organic Chemistry and Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, Lanzhou University, Lanzhou 730000, P. R. China.

l-3,4-Dihydroxy-phenylalanine (l-DOPA) is the most effective drug for the treatment of Parkinson's disease, which plays a very important role in clinical and neurochemistry. However, how to achieve high-sensitivity recognition of l-DOPA still faces challenges. Here, a facile strategy is presented to construct nitrogen-doped chiral CuO/CoO nanofibers (N-CuO/CoO NFs) with nanozyme activity and electrochemiluminescence property, in which CuO/CoO NFs are used as the catalytic activity center and chiral cysteine (Cys) is used as the inducer of chiral recognition, for enantioselective catalysis and sensitive recognition of DOPA enantiomers. Read More

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Fabrication of Homochiral Metal-Organic Frameworks in TiO Nanochannels for Identification of 3,4-Dihydroxyphenylalanine Enantiomers.

Anal Chem 2021 08 11;93(33):11515-11524. Epub 2021 Aug 11.

College of Science, Northeastern University, Shenyang 110004, China.

Enantioselective identification of chiral molecules is important for biomedical and pharmaceutical research. However, owing to identical molecular formulas and chemical properties of enantiomers, signal transduction and amplification are still the two major challenges in chiral sensing. In this study, we developed an enantioselective membrane by integrating homochiral metal-organic frameworks (MOFs) with nanochannels for the sensitive identification and quantification of chiral compounds. Read More

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Kinetic Resolution of Racemic Mixtures via Enantioselective Photocatalysis.

ACS Appl Mater Interfaces 2021 Aug 11;13(33):39781-39790. Epub 2021 Aug 11.

The Russell Berrie Nanotechnology Institute, Technion-Israel Institute of Technology, Haifa 3200003, Israel.

Despite the increasing demand for enantiopure drugs in the pharmaceutical industry, currently available chiral separation technologies are still lagging behind, whether due to throughput or to operability considerations. This paper presents a new kinetic resolution method, based on the specific adsorption of a target enantiomer onto a molecularly imprinted surface of a photocatalyst and its subsequent degradation through a photocatalytic mechanism. The current model system is composed of an active TiO layer, on which the target enantiomer is adsorbed. Read More

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