Substrate-Specific Amino Acid Sensing Using a Molecular d/ l-Cysteine Probe for Comprehensive Stereochemical Analysis in Aqueous Solution

Angewandte Chemie
F Yushra Thanzeel, Christian Wolf

Abstract

The appearance of d-amino acids in mammals and humans has important implications in the life sciences. d/l-Amino acid mixtures play a key role in human physiology and pathology; thus, the introduction of artificial receptors for the real-time quantification of both the concentration and d/l composition of amino acids is very promising for the study of biological processes and for the diagnosis and treatment of diseases. We now report a sensing assay that is compatible with aqueous solutions and allows fast determination of the absolute configuration, enantiomeric composition, and overall amount of cysteine at micromolar concentrations. The method relies on fast UV and CD measurements, which provide accurate stereochemical information on samples covering a wide concentration range and drastically different d/l-cysteine ratios in simulated body fluids. Competition experiments show that other amino acids and biothiols do not interfere with the cysteine-targeted sensing.

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Citations

Apr 13, 2018·Angewandte Chemie·Maria LafuenteIgnacio Alfonso
Sep 14, 2017·Chirality·Zeus A De Los SantosChristian Wolf
Dec 1, 2018·Angewandte Chemie·Zeus A De Los SantosChristian Wolf
Jun 28, 2019·Organic & Biomolecular Chemistry·Samantha L PilicerChristian Wolf
Jul 10, 2019·Chemistry : a European Journal·F Yushra ThanzeelChristian Wolf
Oct 24, 2020·Organic & Biomolecular Chemistry·F Yushra ThanzeelChristian Wolf
Jun 8, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Azam SafarnejadHamid Abdollahi
Jul 31, 2018·Journal of the American Chemical Society·Brenden T HerreraChristian Wolf
Jul 19, 2018·The Journal of Organic Chemistry·Zeus A De Los SantosChristian Wolf
Oct 1, 2019·Journal of the American Chemical Society·F Yushra ThanzeelChristian Wolf

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