Supramolecular Chiral Discrimination of D-Phenylalanine Amino Acid Based on a Perylene Bisimide Derivative

Abstract

The interaction between homochiral substituted perylene bisimide (PBI) molecule and the D enantiomer of phenylalanine amino acid was monitored. Spectroscopic transitions of PBI derivative in aqueous solution in the visible range were used to evaluate the presence of D-phenylalanine. UV-visible, fluorescence, FT-IR, and AFM characterizations showed that D-phenylalanine induces significant variations in the chiral perylene derivative aggregation state and the mechanism is enantioselective as a consequence of the 3D analyte structure. The interaction mechanism was further investigated in presence of interfering amino acid (D-serine and D-histidine) confirming that both chemical structure and its 3D structure play a crucial role for the amino acid discrimination. A D-phenylalanine fluorescence sensor based on perylene was proposed. A limit of detection (LOD) of 64.2 ± 0.38 nM was calculated in the range 10 −7 -10 −5 M and of 1.53 ± 0.89 µM was obtained in the range 10 −5 and 10 −3 M.

Supramolecular Induction of Topological Chirality from Nanoscale Helical Silica Scaffolds to Achiral Molecular Chromophores

“…To this end, chiral polymers, foldamers, or biomolecules such as DNA or peptides have been employed to organize achiral chromophores through covalent − or noncovalent interactions such as H-bonding, hydrophobic, or host–guest binding, , and have been shown to be effective in inducing chirality from one molecule to another. Other studies showed that chiroptical properties could appear upon chiral aggregation of molecules devoid of optical activity in solution. − Tsunega et al have recently reported the use of cationic polymer–anionic chiral counterion assemblies as templates to prepare silica architectures that can induce chiroptical signals to adsorbed dyes and nanocrystals. , Silica with chiral molecular prints has also been used for enantioselective separation/recognition − and has been shown to have the ability to induce chiral arrangement to the achiral molecules adsorbed on its surface . Our previous work has shown that it is possible to induce chiroptical properties to gold nanoparticles or metal complexes organized on the surface of silica nanohelices , or using biphenyl-linked polysilesquioxane through a sol–gel transcription of self-assembled nanohelices from dicationic gemini surfactants.…”

Localized and Surface Plasmons Coupling for Ultrasensitive Dopamine Detection by means of SPR‐Based Perylene Bisimide/Au Nanostructures Thin Film

“…[40] PBI results mainly organized in H aggregates within the thin film, since the A 540 /A 508 value is below 0.9 (black line in Figure 4a). [41] The presence of metallic nanostructures influences the aggregation state of PBI with an inversion of intensity of such bands (purple line in Figure 4a) suggesting a slight change in the aggregates/monomers equilibrium in favor of the monomeric forms.…”

Overview on Multienzymatic Cascades for the Production of Non-canonical α-Amino Acids

“…Among these antibiotics, amoxicillin, cephalexin and ampicillin are included in the World Health Organization's list of essential medicines. D-Phenylalanine is used in the preparation of nateglinide, a drug for the treatment of type 2 diabetes (Bettini et al, 2020). D-valine is used in the synthesis of tau-fluvalinate, a pyrethroid pesticide (Chen et al, 2016).…”