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A dual-mode functional chip for chiral sensing based on mobile phone wettability measurements and portable surface-enhanced Raman spectroscopy (SERS) is reported. The plasmon-active regular gold grating surface was covalently grafted with chiral recognition moieties, l- or d-enantiomers of tartaric acid, making stereoselective discrimination of chiral amines possible. Chiral sensing of amines includes two modes of analysis, performed subsequently on the one chip surface with portable instruments (mobile phone equipped with a camera and developed application (app) Dropangle and a portable Raman spectrometer). First, the wettability changes, caused by enantioselective entrapping of chiral amines, are monitored and analyzed via our mobile phone app, allowing detection of the optical configuration and concentration of enantiomers with 1 order of magnitude accuracy. Second, SERS measurement on the same chip provides information about the chemical structure of entrapped amines and allows calculation of the enantiomeric excess with great accuracy. The applicability of the developed chip is demonstrated on a variety of chiral amines, including tyrosine, cysteine, dopamine (DOPA), and dextromethorphan in analytical solutions and in commercially available DOPA-containing drug. Moreover, we demonstrate that the chips could be regenerated and used repeatedly for at least five cycles.
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http://dx.doi.org/10.1021/acssensors.9b00225 | DOI Listing |
Anal Chem
September 2025
School of Pharmaceutical Sciences, Anhui Medical University, Hefei 230032, China.
Carboxylic enantiomers are prevalent in living organisms and synthetic samples that exhibit important biological properties. The profiling of carboxylic enantiomers is beneficial for monitoring physiological states and further unraveling the metabolism mechanisms between carboxylic enantiomers and diseases. In this study, pairs of light and heavy isotope reagents, ()-(3-aminopiperidin-1-yl) phenyl-methanone/-()-(3-aminopiperidin-1-yl) phenyl-methanone (APMA/-APMA), were synthesized and applied to tag the enantiomers of carboxylic metabolites and drugs.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2025
State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
The enantioselective construction of quaternary carbon stereocenters bearing amine functionalities represents a significant challenge in organic synthesis despite their prevalence in pharmaceutically active compounds. Herein, we report a versatile metallaphotoredox platform for the asymmetric incorporation of amine fragments onto quaternary carbons via coupling of alkene-tethered aryl bromides with readily available α-silylamines. This transformation proceeds under mild conditions without requiring organometallic reagents or stoichiometric reductants.
View Article and Find Full Text PDFChem Commun (Camb)
September 2025
Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, CH-3012 Bern, Switzerland.
Iron complexes bearing chiral salicyloxazoline (Salox) ligands catalyze the enantioselective intramolecular C-H bond amination of alkyl azides, reaching 58-76% ee for benzylic C-H bonds. Further, for the first time aliphatic C-H bond amination is demonstrated (∼40% ee). This class of catalysts even activates primary aliphatic C-H bonds, albeit with moderate ee.
View Article and Find Full Text PDFChemSusChem
September 2025
Organic Chemistry Institute, University of Münster, Corrensstraße 36, 48149, Münster, Germany.
A three-step, one-pot, sequential cascade starting from simple feedstocks to increase complexity toward value-added chiral synthetic building blocks is reported. This is achieved by precisely integrating organic photocatalysis and noncovalent organocatalysis, often operating at dissimilar conditions and reaction media. In particular, this strategy is used to enable the direct transformation of readily available benzylic substrates, such as methylbenzenes, benzyl alcohols, or amines, into enantioenriched α-aminonitriles by benzylic CH photooxidation to their corresponding aldehydes, followed by in situ imine formation and final asymmetric organocatalytic Strecker reaction.
View Article and Find Full Text PDFInorg Chem Front
September 2025
Department of Chemistry, University of Copenhagen Universitetsparken 5 2100 Denmark
We herein demonstrate the synthesis of a pair of enantiomerically pure Yb complexes by post-functionalisation of the parent Yb complex condensation with an enantiomerically pure chiral amine. The enantiomeric pair is structurally characterised by single crystal and powder X-ray diffraction, showing that it crystalises in the 222 Sohncke space group with Flack parameters close to zero, which confirms their enantiopurity. Circular Dichroism (CD) and absorption spectroscopies in the NIR reveal sharp F → F f-f transitions, with values up to 0.
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