Self assembly and gelation in solutions of chiral N-trifluoroacetylated α -aminoalcohols

Стовбун, С. В.; Скоблин, А. А.; Zlenko, Dmitry V.

doi:10.1016/j.chemphys.2018.04.005

Cited by 21 publications

(66 citation statements)

References 43 publications

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“…According with the estimation of the activation energy in the de-assembling process of the aggregates as a consequence of the interaction with D-phenylalanine molecules (Schill et al, 2017;Stovbun et al, 2018;Zlenko et al, 2019a), the binding energy involved for the reported mechanism appears not strong enough (Park and Lee, 2006;Sriramulu and Valiyaveettil, 2016) for inducing a monomerization of D-PBI. The so-called "spontaneous resolution" can be proposed as a cooperative mechanism for justifying the chiral recognition of phenylalanine amino acid (Zlenko et al, 2019b).…”

Section: Disaggregation Process Of D-pbi Aqueous Solution In Presencementioning

confidence: 98%

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

Bettini

Syrgiannis

Ottolini

et al. 2020

Front. Bioeng. Biotechnol.

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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.

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Section: Disaggregation Process Of D-pbi Aqueous Solution In Presencementioning

confidence: 98%

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

Bettini

Syrgiannis

Ottolini

et al. 2020

Front. Bioeng. Biotechnol.

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“…There are a lot of experimental results indicating the role of the exchange interactions in the behavior of the biological systems and their susceptibility to the external magnetic fields: Lipid bilayers tend to align straight across the magnetic field that was interpreted as an effect of the spin polarization and exchange interactions 3 – 9 ; The effect of the chirally-induced spin selectivity was directly observed in the biopolymers 10 , 11 ; The magnetic field effectively inhibits the growth of the supramolecular strings in the solutions of TFAAA-7. Given that the cohesion energy of the monomer in the string is at least 20 kJ/mole (i.e., kT) 33 , while the energy of the interaction of the external field applied with the electrons was only about kT, direct interaction with the magnetic field cannot provide for the effect observed. The exchange interaction seems to be pivotal for the processes of the bio-recognition 9 , 18 and bio-discrimination 38 , which are essential for the modern life and its development 30 , 39 .…”

mentioning

confidence: 99%

“…3 ). TFAAAs form thin ( ) and highly elongated (up to millimeters) helical supramolecular structures called “strings” 33 – 35 . The ultra-thin ( nm) elementary strings twist together to form several heirarchical levels of thicker strings of a diameter up to several microns, and in particular cases—up to 100 32 .…”

mentioning

confidence: 99%

“…However, there was no data on the sensitivity of the strings’ formation to the external magnetic field, while the effects of the spin polarization 10 , 11 , 18 can affect the systems composed of the non-magnetic at the first glance molecules. Moreover, both the strings’ formation 33 and the CISS-based 11 effects are observed only in chirally pure systems, or systems demonstrating spontaneous resolution of enantiomers 35 .

Figure 1 The optical microscope images of the TFAAA strings on the surface of the glass, quartz and mica.…”

mentioning

confidence: 99%

“…However, these difficulties could be in part compensated by accounting for the enantioselective interactions 10 . The quasi-one-dimensional supramolecular strings spontaneously formed by TFAAS have a helical structure and organize into a complex hierarchy of the structural levels sequentially changing the sign of chirality 33 . Such an organization is peculiar for the biological macromolecules 36 , 43 and seems to be forced by the chirality itself.…”

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confidence: 99%

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The weak magnetic field inhibits the supramolecular self-ordering of chiral molecules

Стовбун

Zanin

Скоблин

et al. 2020

Sci Rep

Self Cite

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The magnetic field can affect processes in the non-magnetic systems, including the biochemical reactions in the living cells. This phenomenon becomes possible due to the fermionic nature of an electron and significant energy gain provided by the exchange interactions. Here we report the inhibition effect of the magnetic field on the processes of the chiral supramolecular, i.e., macroscopic self-ordering in the non-magnetic model system. The observed effect is in tune with the reports on the influence of the magnetic field on the adsorption of the chiral molecules, which was explained by the effect of the chirally-induced spin-selectivity and the inhibition of the chemical reactions caused by the singlet-triplet conversion. The magneto sensitivity of the process of the chiral self-ordering directly indicates its spin-polarization nature. Tacking together all of the results in the field, we can propose that the chirality-driven exchange interactions guide the selection of the chiral molecules and explain their prevalence in the living matter. It is also probable that these forces have played a critical role in the origin of life on Earth.

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Triggering gel‐sol transition by weak magnetic field

et al. 2023

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The self‐assembly of small and always chiral molecules into fiber‐like structures is a mysterious process, as the physics underlying such self‐assembly is unclear. The energy necessary for this process exceeds the one provided by common dispersion interactions and hydrogen bonding. The recent results obtained by the scientific group of Prof. Naaman from the Weizmann Institute of Science fed light on the nature of forces providing for the self‐assembly of chiral molecules and attributed these forces to spin‐exchange interactions. Therefore, the self‐assembly of chiral molecules should be magneto‐sensitive. We found such sensitivity in solutions of trifluoroacetylated ‐amino alcohols, and the process was inhibited by the magnetic field when fibers grew on the surface of the substrate. On the contrary, in bulk, the self‐assembly was enhanced by the magnetic field and led to the formation of a dense gel, while no gelation was observed in the absence of the external magnetic field. The latter observations are the theme of this short report, aimed to declare the effect itself but not pretend to describe it in full.

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Self assembly and gelation in solutions of chiral N-trifluoroacetylated α -aminoalcohols

Cited by 21 publications

References 43 publications

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

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

The weak magnetic field inhibits the supramolecular self-ordering of chiral molecules

Triggering gel‐sol transition by weak magnetic field

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