Molecular Recognition of Chiral Zinc Porphyrin with Amino Acid Esters

Wang, Shujun; Ruan, Wen‐Juan; Xin, Zhao; Zhu, Zhaowu

doi:10.1002/cjoc.200590010

Cited by 5 publications

(3 citation statements)

References 15 publications

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“…The molecular recognition of amino acid esters in CHCl 3 was investigated by UV–vis titration with S -tyrosine- [639] and S -threonine [640] substituted chiral zinc porphyrins ( 192 ). The association constants of the molecular recognition reactions were all K R > K S and followed the order of K (PheOMe) > K (LeuOMe) > K (ValOMe) > K (AlaOMe) in host 192a and K (ThrOMe) > K (LeuOMe) > K (ValOMe) > K (AlaOMe) > K (PheOMe) in host 192b .…”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

215

130

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SummaryAmmonium ions are ubiquitous in chemistry and molecular biology. Considerable efforts have been undertaken to develop synthetic receptors for their selective molecular recognition. The type of host compounds for organic ammonium ion binding span a wide range from crown ethers to calixarenes to metal complexes. Typical intermolecular interactions are hydrogen bonds, electrostatic and cation–π interactions, hydrophobic interactions or reversible covalent bond formation. In this review we discuss the different classes of synthetic receptors for organic ammonium ion recognition and illustrate the scope and limitations of each class with selected examples from the recent literature. The molecular recognition of ammonium ions in amino acids is included and the enantioselective binding of chiral ammonium ions by synthetic receptors is also covered. In our conclusion we compare the strengths and weaknesses of the different types of ammonium ion receptors which may help to select the best approach for specific applications.

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Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

215

130

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“…Among the plethora of chiral compounds proposed in the literature to induce chirality into supramolecular porphyrin systems, amino acids are largely used. Apart from porphyrins chemically modified to incorporate amino acid residues [ 57 , 58 , 59 , 60 ], examples of non-covalent approaches, i.e., where chirality is fostered onto self-assembled arrays of achiral porphyrins through simple amino acids added in solution, are less common [ 61 , 62 , 63 , 64 , 65 , 66 ]. Quite recently, Randazzo et al showed that chirality transfer from specific amino acids to porphyrin J-aggregates is a process under hierarchical control [ 47 ].…”

Section: Introductionmentioning

confidence: 99%

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

Zagami

Castriciano

Romeo

et al. 2023

IJMS

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The self-assembling kinetics of the 5,10,15,20-tetrakis(4-sulfonato-phenyl)porphyrin (TPPS4) 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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“…Anyway, many reports in the literature deal with the interaction of simple amino acids with porphyrin receptors. Induction of chirality has been observed in a series of properly functionalized porphyrins, when the contact with the guest amino acid is effective [ 52 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 ]. In this context, it is important to understand whether the TPPS 4 porphyrin, under conditions disfavoring the formation of J-aggregates, is able at monomeric level to form any kind of supramolecular species with a simple amino acid.…”

Section: Introductionmentioning

confidence: 99%

Interaction of Aromatic Amino Acids with Metal Complexes of Tetrakis-(4-Sulfonatophenyl)Porphyrin

Zagami,

Castriciano,

Trapani

et al. 2024

Molecules

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The interaction of a series of metal derivatives of 5, 10, 15, 20-tetrakis(4-sulfonato-phenyl)porphyrin (MTPPS4, M = Cu(II), Pt(II), Ni(II), Zn(II) and Co(II)), including the metal free porphyrin (TPPS4), with the aromatic amino acids L-tryptophan (L-Trp), L-and D-phenylalanine (L-and D-Phe) and L-histidine (L-His) have been investigated through UV/Vis spectroscopy. The amino acid L-serine (L-Ser) has been included as reference compound. The spectroscopic changes induced by adding the amino acids have been exploited to evaluate the extent of interaction between the molecular components in the supramolecular adducts. The binding constants have been estimated for most of the investigated systems, assuming a simple 1:1 equilibrium. The bathochromic shifts of the B-bands, the extent of hypochromicity and the binding constants have been analyzed through two chemical descriptors. All the data point to the important role played by the steric hindrance introduced by axial ligands coordinated to the metal ions and to the degree of hydrophobicity and size of the aromatic moiety in the amino acids.

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Molecular Recognition of Chiral Zinc Porphyrin with Amino Acid Esters

Cited by 5 publications

References 15 publications

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Molecular recognition of organic ammonium ions in solution using synthetic receptors

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

Interaction of Aromatic Amino Acids with Metal Complexes of Tetrakis-(4-Sulfonatophenyl)Porphyrin

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