Water-Soluble Zinc Porphyrins as Receptors for Amino Carboxylates

Imai, Hiroyasu; Misawa, Kazuhisa; Munakata, Hiroki; Uemori, Yoshio

doi:10.1246/cl.2001.688

Cited by 29 publications

(20 citation statements)

References 10 publications

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“…3,17) Proton NMR spectra in D 2 O were obtained from a JEOL JNM-GSX-400 (400 MHz) spectrometer with sodium 3-trimethylsilyl-propanesulfonate as the internal standard. Visible absorption spectra were recorded on a Hitachi U-3000 spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

“…The amino acids were bound to the porphyrins through the coordination of the N atom with the central zinc ion. Additional attractions arise due to Coulomb interactions between the -COO ؊ anion of the amino acids and the -N(CH 3 ) 3 ؉ cation of the porphyrin substituents and due to hydrophobic interactions between the porphyrin plane and the hydrophobic substituents of the amino acids. These attractions could be explained based on the binding data.…”

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confidence: 99%

“…Recently, we synthesized a series of watersoluble zinc porphyrins that show two or more types of attractions for amino acids and peptides. 3,4) These attractions include the coordination interaction and Coulomb interaction, and along with another interaction, these two interactions facilitate amino acid chiral recognition. Coordination interaction is useful as a recognition factor in supramolecular chemistry.…”

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confidence: 99%

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Water-Soluble Zinc Porphyrins as Artificial Receptors for Amino Acids

Imai

Misawa

Munakata

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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The binding of amino acids to water-soluble zinc porphyrins in basic aqueous solution was spectrophotometrically analyzed. The amino acids were bound to the porphyrins through the coordination of the N atom with the central zinc ion. Additional attractions arise due to Coulomb interactions between the -COO ؊ anion of the amino acids and the -N(CH 3 ) 3 ؉ cation of the porphyrin substituents and due to hydrophobic interactions between the porphyrin plane and the hydrophobic substituents of the amino acids. These attractions could be explained based on the binding data. The compensatory relationships of D DS and D DH were also discussed.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Water-Soluble Zinc Porphyrins as Artificial Receptors for Amino Acids

Imai

Misawa

Munakata

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The binding constants were determined based on the published method. 25,26) Synthesis Compound 2 was obtained according to the literature. 25) Compounds 1, 3, and 4 were prepared by methods similar to that for 2.…”

Section: Methodsmentioning

confidence: 99%

“…25,26) Synthesis Compound 2 was obtained according to the literature. 25) Compounds 1, 3, and 4 were prepared by methods similar to that for 2. 5a a,10a a,15b b,20b b-Tetrakis(2-aminophenyl)porphyrinatozinc(II) (5) To a solution of 5a,10a,15b,20b-tetrakis(2-aminophenyl)porphyrin (0.200 g, 0.296 mmol) and 2,6-lutidine (0.30 ml, 1.3 mmol) in tetrahydrofuran (100 ml) was added zinc chloride (0.300 g, 2.20 mmol).…”

Section: Methodsmentioning

confidence: 99%

Binding Enhancements of Nicotinic Acid to Water-Soluble Zinc Porphyrins Based on Triple Attractions of Coordination, Coulomb, and CH-.PI. Interactions

Imai

Munakata

Uemori

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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The examination of the binding of small biomolecules with artificial receptors in aqueous media is one of the traditional approaches to obtain fundamental information on molecular recognition in biological and pharmaceutical conditions. Binding enhancements and selectivity for guests by receptors result from additively and/or cooperatively combined weak non-covalent interactions. Synthetic metalloporphyrins have been widely used as receptors for biomolecules and their analogs; however, not many studies in aqueous solutions [1][2][3][4][5][6][7][8][9][10][11][12] have been reported because of the lipophilic nature of porphyrins. In a previous work, 8) we reported amino acid chiral recognition by a water-soluble zinc porphyrin, where three interactions act as the recognition factors. Two of the interactions are attractive, but the remaining interaction has not yet been identified as attractive or repulsive. Here, we examined the binding behavior of zinc porphyrins 1-4 with amine guests in basic aqueous solutions, where the porphyrin substituents near the central zinc ion can differently interact with the bound guests. The binding data suggested the existence of three types of simultaneous attractive interactions between the zinc porphyrins (2, 4) and the anions of nicotinic acid and 3,5-dicarboxypyridine. Results and DiscussionIn the absence of amine, zinc porphyrins exist as five coordinated species with a bound H 2 O molecule in aqueous solution.13) The N atom of amines is not protonated under the basic experimental conditions (pH 10.4), thereby the N atom of the amines can coordinate to the zinc ion and substitute the bound H 2 O of the porphyrins. The binding equilibrium between zinc porphyrin ZnP and amine L is expressed as follows:where the binding constant is given as Figure 1 shows visible spectra of 4 upon titration of nico. The spectral changes correspond to the N coordination of the The binding of amines to artificial zinc-porphyrin receptors 1-4 was examined in basic aqueous solutions. For nicotinic acid and 3,5-dicarboxypyridine, substantial binding enhancements were observed compared to other amines with no p p system or carboxyl group. This observation suggested that interligand attractions of Coulomb and CH-p p interactions in addition to N-atom coordination can act effectively as recognition factors. The differences in the Coulomb interaction between carboxylate and sulfonate anions were also discussed.

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Reversible Covalent Bond Toolbox

Cheng

Peng

Wang

2012

Supramolecular Chemistry

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In supramolecular chemistry, functional group interactions play a critical role. The use of covalent interactions, however, is not as common as noncovalent interactions mostly because of their irreversible nature. This chapter covers those covalent interactions that are readily reversible and are often used in the construction of supramolecular assemblies and sensor design. Especially important in such work are boronic acid interactions with diols and other nucleophiles/Lewis bases, anion–metal interactions, and aldehyde–amine/alcohol interactions because of their ready reversibility.

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Water-Soluble Zinc Porphyrins as Receptors for Amino Carboxylates

Cited by 29 publications

References 10 publications

Water-Soluble Zinc Porphyrins as Artificial Receptors for Amino Acids

Water-Soluble Zinc Porphyrins as Artificial Receptors for Amino Acids

Binding Enhancements of Nicotinic Acid to Water-Soluble Zinc Porphyrins Based on Triple Attractions of Coordination, Coulomb, and CH-.PI. Interactions

Reversible Covalent Bond Toolbox

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