2018
DOI: 10.3390/molecules24010084
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Chiral Recognition of L- and D- Amino Acid by Porphyrin Supramolecular Aggregates

Abstract: We report of the interactions between four amino acids lysine (Lys), arginine (Arg), histidine (His), and phenylalanine (Phe) with the J-aggregates of the protonated 5,10,15,20-tetrakis(4-sulfonatophenyl)-porphyrin H4TPPS. Several aspects of these self-assembled systems have been analyzed: (i) the chiral transfer process; (ii) the hierarchical effects leading to the aggregates formation; and, (iii) the influence of the amino acid concentrations on both transferring and storing chiral information. We have demon… Show more

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Cited by 32 publications
(34 citation statements)
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“…Under specific experimental conditions (pH, ionic strength, concentration, etc. ), protonated H 2 TPPS self-assemble into H- and J-aggregates of different shapes and sizes (Randazzo et al, 2018 ).…”
Section: Resultsmentioning
confidence: 99%
“…Under specific experimental conditions (pH, ionic strength, concentration, etc. ), protonated H 2 TPPS self-assemble into H- and J-aggregates of different shapes and sizes (Randazzo et al, 2018 ).…”
Section: Resultsmentioning
confidence: 99%
“…[11][12][13][14][15][16][17][18] Usually, chiroptical properties could arise from the presence of stereogenic centers in the basic building blocks, [19][20][21][22][23][24][25] or induced by a chiral scaffold or chemical template, such as simple chiral compounds, polymers and biomolecules. [26][27][28][29][30][31][32][33][34][35] Many examples of J-aggregated TPPS4 exhibiting optical activity under the presence of chemical [36][37][38][39][40][41][42][43][44][45][46][47] or physical chiral bias [48][49][50][51][52][53][54][55] have been reported so far. The occurrence of spontaneous symmetry breaking during the growth process has been related to kinetics and in particular to mixing protocols.…”
Section: Introductionmentioning
confidence: 99%
“…When TPPS (5 μM) was added to the AuNCs solution, the electronic spectrum for both histidine enantiomers showed the presence of a porphyrin Soret band centered at 418 nm and four bands located in the visible region at 517, 554, 587, and 642 nm (red spectrum, Figure 1). The positions of both the B and visible bands were bathochromically shifted compared to those of the free base TPPS in aqueous solution in the presence of histidine [51].…”
Section: Resultsmentioning
confidence: 99%
“…The low induced CD intensity was in line with the monomeric nature of the chromophore. Recently, it has been reported that no interaction between TPPS and histidine has been detected in aqueous solution, mainly due to electrostatic repulsions between the negatively charged porphyrins and the amino acids [51].…”
Section: Resultsmentioning
confidence: 99%