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Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates

The self-assembling kinetics of the 5,10,15,20-tetrakis(4-sulfonato-phenyl)porphyrin (TPPS(4)) into nano-tubular J-aggregates under strong acidic condition and in the presence of amino acids as templating chiral reagents have been investigated through UV/Vis spectroscopy. The ability of the chiral s...

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Autores principales: Zagami, Roberto, Castriciano, Maria Angela, Romeo, Andrea, Scolaro, Luigi Monsù
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9860692/
https://www.ncbi.nlm.nih.gov/pubmed/36675210
http://dx.doi.org/10.3390/ijms24021695
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author Zagami, Roberto
Castriciano, Maria Angela
Romeo, Andrea
Scolaro, Luigi Monsù
author_facet Zagami, Roberto
Castriciano, Maria Angela
Romeo, Andrea
Scolaro, Luigi Monsù
author_sort Zagami, Roberto
collection PubMed
description The self-assembling kinetics of the 5,10,15,20-tetrakis(4-sulfonato-phenyl)porphyrin (TPPS(4)) into nano-tubular J-aggregates under strong acidic condition and in the presence of amino acids as templating chiral reagents have been investigated through UV/Vis spectroscopy. The ability of the chiral species to transfer its chiral information to the final J-aggregate has been measured through circular dichroism (CD) spectroscopy and compared to the spontaneous symmetry breaking process usually observed in these nano-aggregates. Under the experimental conditions here selected, including mixing protocol, we have observed a large difference in the observed aggregation rates for the various amino acids, those with a positively charged side group being the most effective. On the contrary, these species are less efficient in transferring their chirality, exhibiting a quite low or modest enhancement in the observed dissymmetry g-factors. On the other side, hydrophobic and some hydrophilic amino acids are revealed to be very active in inducing chirality with a discrete increase of intensity of the detected CD bands with respect to the spontaneous symmetry breaking.
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spelling pubmed-98606922023-01-22 Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates Zagami, Roberto Castriciano, Maria Angela Romeo, Andrea Scolaro, Luigi Monsù Int J Mol Sci Article The self-assembling kinetics of the 5,10,15,20-tetrakis(4-sulfonato-phenyl)porphyrin (TPPS(4)) into nano-tubular J-aggregates under strong acidic condition and in the presence of amino acids as templating chiral reagents have been investigated through UV/Vis spectroscopy. The ability of the chiral species to transfer its chiral information to the final J-aggregate has been measured through circular dichroism (CD) spectroscopy and compared to the spontaneous symmetry breaking process usually observed in these nano-aggregates. Under the experimental conditions here selected, including mixing protocol, we have observed a large difference in the observed aggregation rates for the various amino acids, those with a positively charged side group being the most effective. On the contrary, these species are less efficient in transferring their chirality, exhibiting a quite low or modest enhancement in the observed dissymmetry g-factors. On the other side, hydrophobic and some hydrophilic amino acids are revealed to be very active in inducing chirality with a discrete increase of intensity of the detected CD bands with respect to the spontaneous symmetry breaking. MDPI 2023-01-15 /pmc/articles/PMC9860692/ /pubmed/36675210 http://dx.doi.org/10.3390/ijms24021695 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zagami, Roberto
Castriciano, Maria Angela
Romeo, Andrea
Scolaro, Luigi Monsù
Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates
title Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates
title_full Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates
title_fullStr Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates
title_full_unstemmed Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates
title_short Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates
title_sort kinetic investigations on the chiral induction by amino acids in porphyrin j-aggregates
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9860692/
https://www.ncbi.nlm.nih.gov/pubmed/36675210
http://dx.doi.org/10.3390/ijms24021695
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