Stereoselective Sensing of l‐ and d‐Amino Acids: Development of a Fluorescence‐Array Based on Readily Available Chiral Phosphoric Acids

Abstract

The identification of structurally related analytes has become possible using sensor arrays, based on sets of cross‐reactive chemosensors. This work reports the use of readily available chiral phosphoric acids for the array‐based, chemo‐ and stereoselective sensing of l‐ and d‐amino acids. Six bis‐ and trisphosphoric acids were used in combination with Ni2+ and Eu3+, resulting in a set of twelve chiral fluorescent chemosensors. This sensor‐array enables a correct classification of l‐amino acids with 100 % accuracy, while the differentiation between l‐ and d‐amino acids can be achieved with 94 % accuracy. In addition, the systematic analysis of sensor contributions has allowed the use of a reduced set of seven sensors for the classification of l‐amino acids, thus drastically reducing the amount of necessary measurements.

Enantioselective Fluorescent Recognition of Free Amino Acids: Challenges and Opportunities

“…The reaction of amino acids with binaphthyl‐based perfluoroalkyl ketones led to enantioselective fluorescent responses [9h,i] . Binaphthyl phosphoric acids in combination with Ni 2+ or Eu 3+ ions were used to detect amino acids [9j] . Among the various binaphthyl‐based fluorescent probes, those using aldehyde groups as the amino acid binding sites have been systematically investigated in recent years, and are discussed in more detail in this section.…”

Easy-to-Prepare Mini-Chemosensor Array for Simultaneous Detection of Cysteine and Glutathione Derivatives

“…Furthermore, the arrays constructed by the chemosensors allow classification and quantification of multianalytes. Previously, several examples of chemosensor arrays for natural amino acids, − SCAAs, , and proteins , were reported. However, the arrays require a number of chemosensors obtained via multiple and complicated organic syntheses, which reduce their popularity in real-world scenarios. − …”

Cooperative Organocatalysis: A Systematic Investigation of Covalently Linked Organophosphoric Acids for the Stereoselective Transfer Hydrogenation of Quinolines

“…While these were already successfully applied in chemosensing, e.g. for the binding and detection of metal‐ions[16a] and amino‐acids,, [16b] we have now for the first time investigated their use in asymmetric Brønsted‐acid catalysis. Using the transfer‐hydrogenation of quinolines as a test reaction, we set out to elucidate the influence of the relative orientation of the phosphoric acids ( 1d vs. 1e ) and the overall number of acidic groups ( 1d / e vs. 1f ) on the catalytic reaction.…”