Importance of hydrogen‐bonding sites in the chiral recognition mechanism between racemic D3 terbium(III) complexes and amino acids
Identifieur interne : 001010 ( Main/Curation ); précédent : 001009; suivant : 001011Importance of hydrogen‐bonding sites in the chiral recognition mechanism between racemic D3 terbium(III) complexes and amino acids
Auteurs : Ahmed Moussa [États-Unis] ; Christine Pham [États-Unis] ; Shruthi Bommireddy [États-Unis] ; Gilles Muller [États-Unis]Source :
- Chirality [ 0899-0042 ] ; 2009-05.
Descripteurs français
- Wicri :
- topic : Acide.
English descriptors
- KwdEn :
- Absolute stereochemistry, Acid, Active sites, Amino, Amino acid, Amino acids, Amino group, Analog compound, Aqueous solution, Aqueous solutions, Aromatic rings, Brittain, Carbon atoms, Carboxylate function, Carboxylic acids, Chelidamic acid, Chem, Chemical shifts, Chiral, Chiral agents, Chiral lanthanide complexes, Chiral molecules, Chiral probe, Chiral probes, Chiral recognition, Chirality, Circular dichroism, Circularly, Complex salts, Contract grant number, Coord chem, Coulombic forces, Dalton trans, Diastereomeric association, Drug discovery, Emission monochromator, Emission spectra, Equilibrium shift, Excitation, Excitation spectra, Excitation wavelengths, Experimental conditions, Form hydrogen bonds, Free unassociated, Gilles muller, Glum, Glum values, Guanidino group, High degree, Hydrophobic effects, Hydroxyl, Hydroxyl group, Inorg, Inorg chem, Jose state university, Lanthanide, Lanthanide complexes, Ligand, Ligand interface, Ligand ratio, Local structure, Luminescence, Luminescence dissymmetry factor, Luminescence dissymmetry ratio values, Luminescence spectroscopy, Luminescence studies, Opposite signs, Optical activity, Optical rotation values, Other hand, Perturbation, Pfeiffer, Pfeiffer effect, Positive charge, Practical guide, Preferential formation, Pyridine ring, Pyrrolidone rings, Racemic, Racemic complexes, Racemic equilibrium, Racemic mixtures, Racemic solution, Racemic solutions, Recognition mechanism, Side chain, Spectral range, Spectroscopic studies, Standard deviation, Various acids, Washington square, Zwitterionic form.
- Teeft :
- Absolute stereochemistry, Acid, Active sites, Amino, Amino acid, Amino acids, Amino group, Analog compound, Aqueous solution, Aqueous solutions, Aromatic rings, Brittain, Carbon atoms, Carboxylate function, Carboxylic acids, Chelidamic acid, Chem, Chemical shifts, Chiral, Chiral agents, Chiral lanthanide complexes, Chiral molecules, Chiral probe, Chiral probes, Chiral recognition, Chirality, Circular dichroism, Circularly, Complex salts, Contract grant number, Coord chem, Coulombic forces, Dalton trans, Diastereomeric association, Drug discovery, Emission monochromator, Emission spectra, Equilibrium shift, Excitation, Excitation spectra, Excitation wavelengths, Experimental conditions, Form hydrogen bonds, Free unassociated, Gilles muller, Glum, Glum values, Guanidino group, High degree, Hydrophobic effects, Hydroxyl, Hydroxyl group, Inorg, Inorg chem, Jose state university, Lanthanide, Lanthanide complexes, Ligand, Ligand interface, Ligand ratio, Local structure, Luminescence, Luminescence dissymmetry factor, Luminescence dissymmetry ratio values, Luminescence spectroscopy, Luminescence studies, Opposite signs, Optical activity, Optical rotation values, Other hand, Perturbation, Pfeiffer, Pfeiffer effect, Positive charge, Practical guide, Preferential formation, Pyridine ring, Pyrrolidone rings, Racemic, Racemic complexes, Racemic equilibrium, Racemic mixtures, Racemic solution, Racemic solutions, Recognition mechanism, Side chain, Spectral range, Spectroscopic studies, Standard deviation, Various acids, Washington square, Zwitterionic form.
Abstract
The perturbation of the racemic equilibrium of luminescent D3 terbium(III) complexes with chelidamic acid (CDA), a hydroxylated derivative of 2,6‐pyridine‐dicarboxylic acid (DPA), by added chiral biomolecules such as L‐amino acids has been studied using circularly polarized luminescence and 13C NMR spectroscopy. It is shown in this work that the chiral‐induced equilibrium shift of [Tb(CDA)3]6− by L‐amino acids (i.e. L‐proline or L‐arginine) was largely influenced by the hydrogen‐bonding networks formed between the ligand interface of racemic [Tb(CDA)3]6− and these added chiral agents. The capping of potential hydrogen‐bonding sites by acetylation in L‐proline led to a ∼100‐fold drop in the induced optical activity of the [Tb(CDA)3]6−:N‐acetyl‐L‐proline system. This result suggested that the hydrogen‐bonding networks serve as the basis for further noncovalent discriminatory interactions between racemic [Tb(CDA)3]6− and added L‐amino acids. Chirality, 2009. © 2008 Wiley‐Liss, Inc.
Url:
- https://api.istex.fr/document/0E84689966BCA756674BA0BDCF53826BC9F114B0/fulltext/pdf
- http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2668746
DOI: 10.1002/chir.20628
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<term>Acid</term>
<term>Active sites</term>
<term>Amino</term>
<term>Amino acid</term>
<term>Amino acids</term>
<term>Amino group</term>
<term>Analog compound</term>
<term>Aqueous solution</term>
<term>Aqueous solutions</term>
<term>Aromatic rings</term>
<term>Brittain</term>
<term>Carbon atoms</term>
<term>Carboxylate function</term>
<term>Carboxylic acids</term>
<term>Chelidamic acid</term>
<term>Chem</term>
<term>Chemical shifts</term>
<term>Chiral</term>
<term>Chiral agents</term>
<term>Chiral lanthanide complexes</term>
<term>Chiral molecules</term>
<term>Chiral probe</term>
<term>Chiral probes</term>
<term>Chiral recognition</term>
<term>Chirality</term>
<term>Circular dichroism</term>
<term>Circularly</term>
<term>Complex salts</term>
<term>Contract grant number</term>
<term>Coord chem</term>
<term>Coulombic forces</term>
<term>Dalton trans</term>
<term>Diastereomeric association</term>
<term>Drug discovery</term>
<term>Emission monochromator</term>
<term>Emission spectra</term>
<term>Equilibrium shift</term>
<term>Excitation</term>
<term>Excitation spectra</term>
<term>Excitation wavelengths</term>
<term>Experimental conditions</term>
<term>Form hydrogen bonds</term>
<term>Free unassociated</term>
<term>Gilles muller</term>
<term>Glum</term>
<term>Glum values</term>
<term>Guanidino group</term>
<term>High degree</term>
<term>Hydrophobic effects</term>
<term>Hydroxyl</term>
<term>Hydroxyl group</term>
<term>Inorg</term>
<term>Inorg chem</term>
<term>Jose state university</term>
<term>Lanthanide</term>
<term>Lanthanide complexes</term>
<term>Ligand</term>
<term>Ligand interface</term>
<term>Ligand ratio</term>
<term>Local structure</term>
<term>Luminescence</term>
<term>Luminescence dissymmetry factor</term>
<term>Luminescence dissymmetry ratio values</term>
<term>Luminescence spectroscopy</term>
<term>Luminescence studies</term>
<term>Opposite signs</term>
<term>Optical activity</term>
<term>Optical rotation values</term>
<term>Other hand</term>
<term>Perturbation</term>
<term>Pfeiffer</term>
<term>Pfeiffer effect</term>
<term>Positive charge</term>
<term>Practical guide</term>
<term>Preferential formation</term>
<term>Pyridine ring</term>
<term>Pyrrolidone rings</term>
<term>Racemic</term>
<term>Racemic complexes</term>
<term>Racemic equilibrium</term>
<term>Racemic mixtures</term>
<term>Racemic solution</term>
<term>Racemic solutions</term>
<term>Recognition mechanism</term>
<term>Side chain</term>
<term>Spectral range</term>
<term>Spectroscopic studies</term>
<term>Standard deviation</term>
<term>Various acids</term>
<term>Washington square</term>
<term>Zwitterionic form</term>
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<keywords scheme="Teeft" xml:lang="en"><term>Absolute stereochemistry</term>
<term>Acid</term>
<term>Active sites</term>
<term>Amino</term>
<term>Amino acid</term>
<term>Amino acids</term>
<term>Amino group</term>
<term>Analog compound</term>
<term>Aqueous solution</term>
<term>Aqueous solutions</term>
<term>Aromatic rings</term>
<term>Brittain</term>
<term>Carbon atoms</term>
<term>Carboxylate function</term>
<term>Carboxylic acids</term>
<term>Chelidamic acid</term>
<term>Chem</term>
<term>Chemical shifts</term>
<term>Chiral</term>
<term>Chiral agents</term>
<term>Chiral lanthanide complexes</term>
<term>Chiral molecules</term>
<term>Chiral probe</term>
<term>Chiral probes</term>
<term>Chiral recognition</term>
<term>Chirality</term>
<term>Circular dichroism</term>
<term>Circularly</term>
<term>Complex salts</term>
<term>Contract grant number</term>
<term>Coord chem</term>
<term>Coulombic forces</term>
<term>Dalton trans</term>
<term>Diastereomeric association</term>
<term>Drug discovery</term>
<term>Emission monochromator</term>
<term>Emission spectra</term>
<term>Equilibrium shift</term>
<term>Excitation</term>
<term>Excitation spectra</term>
<term>Excitation wavelengths</term>
<term>Experimental conditions</term>
<term>Form hydrogen bonds</term>
<term>Free unassociated</term>
<term>Gilles muller</term>
<term>Glum</term>
<term>Glum values</term>
<term>Guanidino group</term>
<term>High degree</term>
<term>Hydrophobic effects</term>
<term>Hydroxyl</term>
<term>Hydroxyl group</term>
<term>Inorg</term>
<term>Inorg chem</term>
<term>Jose state university</term>
<term>Lanthanide</term>
<term>Lanthanide complexes</term>
<term>Ligand</term>
<term>Ligand interface</term>
<term>Ligand ratio</term>
<term>Local structure</term>
<term>Luminescence</term>
<term>Luminescence dissymmetry factor</term>
<term>Luminescence dissymmetry ratio values</term>
<term>Luminescence spectroscopy</term>
<term>Luminescence studies</term>
<term>Opposite signs</term>
<term>Optical activity</term>
<term>Optical rotation values</term>
<term>Other hand</term>
<term>Perturbation</term>
<term>Pfeiffer</term>
<term>Pfeiffer effect</term>
<term>Positive charge</term>
<term>Practical guide</term>
<term>Preferential formation</term>
<term>Pyridine ring</term>
<term>Pyrrolidone rings</term>
<term>Racemic</term>
<term>Racemic complexes</term>
<term>Racemic equilibrium</term>
<term>Racemic mixtures</term>
<term>Racemic solution</term>
<term>Racemic solutions</term>
<term>Recognition mechanism</term>
<term>Side chain</term>
<term>Spectral range</term>
<term>Spectroscopic studies</term>
<term>Standard deviation</term>
<term>Various acids</term>
<term>Washington square</term>
<term>Zwitterionic form</term>
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<front><div type="abstract" xml:lang="en">The perturbation of the racemic equilibrium of luminescent D3 terbium(III) complexes with chelidamic acid (CDA), a hydroxylated derivative of 2,6‐pyridine‐dicarboxylic acid (DPA), by added chiral biomolecules such as L‐amino acids has been studied using circularly polarized luminescence and 13C NMR spectroscopy. It is shown in this work that the chiral‐induced equilibrium shift of [Tb(CDA)3]6− by L‐amino acids (i.e. L‐proline or L‐arginine) was largely influenced by the hydrogen‐bonding networks formed between the ligand interface of racemic [Tb(CDA)3]6− and these added chiral agents. The capping of potential hydrogen‐bonding sites by acetylation in L‐proline led to a ∼100‐fold drop in the induced optical activity of the [Tb(CDA)3]6−:N‐acetyl‐L‐proline system. This result suggested that the hydrogen‐bonding networks serve as the basis for further noncovalent discriminatory interactions between racemic [Tb(CDA)3]6− and added L‐amino acids. Chirality, 2009. © 2008 Wiley‐Liss, Inc.</div>
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