Stability Constants of Picolinic and Quinaldic Acid Chelates of Bivalent Metals.

Suzuki, K.; Yasuda, Mikio; Yamasaki, Kazuo

doi:10.1021/j150548a017

Cited by 60 publications

(28 citation statements)

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“…The resemblance of structural features of PQQ and well-known chelating agents, for example, α-picolinic acid 57 and 8-hydroxyquinoline 58 has been noticed in an early stage. Two positions for chelation seem available to divalent cations: (1) between the two carbonyl groups, or (2) between the C(5)-carbonyl and C(7)-carboxylic acid group.…”

Section: Role Of Calciummentioning

confidence: 99%

Direct hydride transfer in the reaction mechanism of quinoprotein alcohol dehydrogenases: a quantum mechanical investigation

Jongejan

Hagen

2001

J Comput Chem

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Oxidation of alcohols by direct hydride transfer to the pyrroloquinoline quinone (PQQ) cofactor of quinoprotein alcohol dehydrogenases has been studied using ab initio quantum mechanical methods. Energies and geometries were calculated at the 6-31G(d,p) level of theory. Comparison of the results obtained for PQQ and several derivatives with available structural and spectroscopic data served to judge the feasibility of the calculations. The role of calcium in the enzymatic reaction mechanism has been investigated. Transition state searches have been conducted at the semiempirical and STO-3G(d) level of theory. It is concluded that hydride transfer from the Calpha-position of the substrate alcohol (or aldehyde) directly to the C(5) carbon of PQQ is energetically feasible. Copyright 2001 John Wiley & Sons, Inc. J Comput Chem 22: 1732-1749, 2001

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Section: Role Of Calciummentioning

confidence: 99%

Direct hydride transfer in the reaction mechanism of quinoprotein alcohol dehydrogenases: a quantum mechanical investigation

Jongejan

Hagen

2001

J Comput Chem

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“…Pyridinecarboxylic acids (picolinic, nicotinic and isonicotinic) are biologically important ligands incorporated into some enzymes, and they are active agents in some drugs as well [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. In our previous work, we examined the effect of different metals (alkali [19][20][21], alkaline earth [22], 3d-metals [23]) on the electronic system of pyridinecarboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic (IR, Raman) and thermogravimetric studies of 3d-metal cinchomeronates and dinicotinates

Świderski

Kalinowska

Rusinek³

et al. 2016

J Therm Anal Calorim

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In this work, the thermal and spectroscopic properties of 3d-metal (Co, Cu, Zn, Mn, Ni, Fe) and sodium salts with cinchomeronic acid (3,4-pyridinedicarboxylic acid) (3,4pda) and dinicotinic acid (3,5-pyridinedicarboxylic acid) (3,5pda) were studied. The IR and Raman spectra were registered and analyzed in the range of 400-4000 cm -1 . The thermogravimetric study of synthesized compounds was done. The degree of hydration and the products of thermal decomposition were estimated. Moreover, it was done the comparison between the effect of 3d-transition metal cations and sodium cation on the degree of perturbation or stabilization of the electronic system of pyridine molecule depending on the position of carboxylic group in the ring.

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“…Picolinic acid is known to be a bidentate chelating ligand (16,17). Paul et al (14) as well as Clark and Williams (2, 3) have proven that picolinic acid-metal complexes are formed by coordination with the pyridine nitrogen and the carbonyl oxygen on the adjacent carboxylic acid group.…”

Section: Discussionmentioning

confidence: 99%

“…constants for zinc and picolinic acid determined by Suzuki et al (16) and von Anderegg (17) are respectively: log k, = 5.12 and 5.3; log Kz = 4.3 and 4.32; and log K = 9.42 and 9.63. The concentration of picolinic acid in human milk is approximately 300 pM whereas the concentration of zinc in human milk is generally less than 100 pM (10).…”

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confidence: 91%

Characterization and Quantitation of a Zinc-Binding Ligand in Human Milk

Evans

Johnson

1980

Pediatric Research

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SummaryA low-molecular-weight zinc-binding ligand from human milk has been isolated and characterized. The ligand was isolated by chromatography on Dowex 50, Dowex 1, and Sephadex G-15 equilibrated with 0.153 mM Zn(N03)2. Mass spectroscopy, thinlayer chromatography, and infrared spectroscopy proved that the zinc-binding ligand isolated by this method from human milk is pyridine-2-carboxylic acid, commonly known as picolinic acid. The concentration of picolinic acid in human milk was 308 pM, the concentration in one brand of processed cow's milk was 20 pM, but picolinic acid was undetectable in a second brand of cow's milk and in four different infant formulas. Weanling rats fed supplemental picolinic acid absorbed significantly more dietary zinc and gained significantly more weight than rats fed an unsupplemented diet. The results suggest that the high bioavailability of zinc in human milk results from the presence of picolinic acid, a bidentate chelating ligand which facilitates zinc absorption from the intestine. SpeculationThe high bioavailability of zinc in human milk results from the presence of picolinic acid, a bidentate chelating ligand which facilitates zinc absorption from the intestine.Several clinical observations demonstrate that the bioavailability of zinc from human milk is much greater than that from cow's milk. In children affected with acrodermatitis enteropathica, an inherited disease that affects zinc metabolism (8), the symptoms characteristic of the disease do not generally appear until the child is weaned from the breast (1, 4, 5). Human milk has also been used successfully in the treatment of acrodermatitis enteropathica (15). Hambidge et al. (9) found that the plasma zinc concentration of breast-fed infants is not significantly different than that of healthy young adults. In contrast, the plasma zinc concentration of infants fed either zinc-supplemented formula or non-zinc-supplemented formula is significantly less than that of young adults. These observations suggest that human milk may contain a ligand or ligands which facilitate zinc absorption.To date, attempts to isolate zinc-binding ligands from biologic fluids have not been successful due to the fact that investigators have consistently used classical gel filtration chromatography. The problems encountered when attempting to detect and identify zinc-chelating ligands by the use of classical gel filtration have been discussed by Evans et al. (6). These authors have also described a technique, referred to as modified gel filtration chromatography, which can be used to reproducibly detect zinc-binding ligands in biologic fluids. This technique has now been adapted to isolate and quantitate a zinc-binding ligand in human milk. MATERIALS AND METHODS DETECTION OF ZINC-BINDING LIGANDSified gel filtration chromatography. A glass column 1.5 x 90 crr was packed with 44.4 g Sephadex G-15 (Pharmacia Fine Chemi. cals, Inc.) (18). The gel was equilibrated with 50 mM Tris acetate pH 7.4, that contained 0.1% NaN3 and 0.153 mM Zn(NO3)z. Thc buffer...

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Stability Constants of Picolinic and Quinaldic Acid Chelates of Bivalent Metals.

Cited by 60 publications

References 0 publications

Direct hydride transfer in the reaction mechanism of quinoprotein alcohol dehydrogenases: a quantum mechanical investigation

Direct hydride transfer in the reaction mechanism of quinoprotein alcohol dehydrogenases: a quantum mechanical investigation

Spectroscopic (IR, Raman) and thermogravimetric studies of 3d-metal cinchomeronates and dinicotinates

Characterization and Quantitation of a Zinc-Binding Ligand in Human Milk

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