Importance of hydrogen‐bonding sites in the chiral recognition mechanism between racemic D3 terbium(III) complexes and amino acids
Identifieur interne : 000305 ( Istex/Corpus ); précédent : 000304; suivant : 000306Importance of hydrogen‐bonding sites in the chiral recognition mechanism between racemic D3 terbium(III) complexes and amino acids
Auteurs : Ahmed Moussa ; Christine Pham ; Shruthi Bommireddy ; Gilles MullerSource :
- Chirality [ 0899-0042 ] ; 2009-05.
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:
DOI: 10.1002/chir.20628
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ISTEX:0E84689966BCA756674BA0BDCF53826BC9F114B0Le document en format XML
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95192‐0101</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Chirality</title><title level="j" type="alt">CHIRALITY</title><idno type="ISSN">0899-0042</idno><idno type="eISSN">1520-636X</idno><imprint><biblScope unit="vol">21</biblScope><biblScope unit="issue">5</biblScope><biblScope unit="page" from="497">497</biblScope><biblScope unit="page" to="506">506</biblScope><biblScope unit="page-count">10</biblScope><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><pubPlace>Hoboken</pubPlace><date type="published" when="2009-05">2009-05</date></imprint><idno type="ISSN">0899-0042</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0899-0042</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" 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></keywords><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 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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. 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95192‐0101</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>circularly polarized luminescence</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>lanthanide</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>chirality</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>amino acid</value></json:item></subject><articleId><json:string>CHIR20628</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>article</json:string></originalGenre><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. 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type="main" xml:lang="en">Importance of hydrogen‐bonding sites in the chiral recognition mechanism between racemic D<hi rend="subscript">3</hi> terbium(III) complexes and amino acids</title><title level="a" type="short" xml:lang="en">Chiral Recognition of Amino Acids Using CPL</title><author xml:id="author-0000"><persName><forename type="first">Ahmed</forename><surname>Moussa</surname></persName><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, California<address><country key="US"></country></address></affiliation></author><author xml:id="author-0001"><persName><forename type="first">Christine</forename><surname>Pham</surname></persName><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, California<address><country key="US"></country></address></affiliation></author><author xml:id="author-0002"><persName><forename type="first">Shruthi</forename><surname>Bommireddy</surname></persName><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, California<address><country key="US"></country></address></affiliation></author><author xml:id="author-0003" role="corresp"><persName><forename type="first">Gilles</forename><surname>Muller</surname></persName><email>gilles.muller@sjsu.edu</email><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, California<address><country key="US"></country></address></affiliation><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, CA 95192‐0101</affiliation></author><idno type="istex">0E84689966BCA756674BA0BDCF53826BC9F114B0</idno><idno type="ark">ark:/67375/WNG-4D4FFG2K-M</idno><idno type="DOI">10.1002/chir.20628</idno><idno type="unit">CHIR20628</idno><idno type="toTypesetVersion">file:CHIR.CHIR20628.pdf</idno></analytic><monogr><title level="j" type="main">Chirality</title><title level="j" type="alt">CHIRALITY</title><idno type="pISSN">0899-0042</idno><idno type="eISSN">1520-636X</idno><idno type="book-DOI">10.1002/(ISSN)1520-636X</idno><idno type="book-part-DOI">10.1002/chir.v21:5</idno><idno type="product">CHIR</idno><imprint><biblScope unit="vol">21</biblScope><biblScope unit="issue">5</biblScope><biblScope unit="page" from="497">497</biblScope><biblScope unit="page" to="506">506</biblScope><biblScope unit="page-count">10</biblScope><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><pubPlace>Hoboken</pubPlace><date type="published" when="2009-05"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><abstract xml:lang="en" style="main"><head>Abstract</head><p>The perturbation of the racemic equilibrium of luminescent D<hi rend="subscript">3</hi> terbium(III) complexes with chelidamic acid (CDA), a hydroxylated derivative of 2,6‐pyridine‐dicarboxylic acid (DPA), by added chiral biomolecules such as <hi rend="smallCaps">L</hi>‐amino acids has been studied using circularly polarized luminescence and <hi rend="superscript">13</hi>C NMR spectroscopy. It is shown in this work that the chiral‐induced equilibrium shift of [Tb(CDA)<hi rend="subscript">3</hi>]<hi rend="superscript">6−</hi> by <hi rend="smallCaps">L</hi>‐amino acids (i.e. <hi rend="smallCaps">L</hi>‐proline or <hi rend="smallCaps">L</hi>‐arginine) was largely influenced by the hydrogen‐bonding networks formed between the ligand interface of racemic [Tb(CDA)<hi rend="subscript">3</hi>]<hi rend="superscript">6−</hi> and these added chiral agents. The capping of potential hydrogen‐bonding sites by acetylation in <hi rend="smallCaps">L</hi>‐proline led to a ∼100‐fold drop in the induced optical activity of the [Tb(CDA)<hi rend="subscript">3</hi>]<hi rend="superscript">6−</hi>:<hi rend="italic">N</hi>‐acetyl‐<hi rend="smallCaps">L</hi>‐proline system. This result suggested that the hydrogen‐bonding networks serve as the basis for further noncovalent discriminatory interactions between racemic [Tb(CDA)<hi rend="subscript">3</hi>]<hi rend="superscript">6−</hi> and added <hi rend="smallCaps">L</hi>‐amino acids. Chirality, 2009. © 2008 Wiley‐Liss, Inc.</p></abstract><textClass><keywords xml:lang="en"><term xml:id="kwd1">circularly polarized luminescence</term><term xml:id="kwd2">lanthanide</term><term xml:id="kwd3">chirality</term><term xml:id="kwd4">amino acid</term></keywords><keywords rend="articleCategory"><term>Regular Article</term></keywords><keywords rend="tocHeading1"><term>Regular Articles</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/0E84689966BCA756674BA0BDCF53826BC9F114B0/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" 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position="30" status="forIssue"><doi origin="wiley" registered="yes">10.1002/chir.20628</doi><idGroup><id type="unit" value="CHIR20628"></id></idGroup><countGroup><count type="pageTotal" number="10"></count></countGroup><titleGroup><title type="articleCategory">Regular Article</title><title type="tocHeading1">Regular Articles</title></titleGroup><copyright ownership="publisher">Copyright © 2008 Wiley‐Liss, Inc.</copyright><eventGroup><event type="manuscriptReceived" date="2008-02-28"></event><event type="manuscriptAccepted" date="2008-05-28"></event><event type="publishedOnlineEarlyUnpaginated" date="2008-08-12"></event><event type="firstOnline" date="2008-08-12"></event><event type="publishedOnlineFinalForm" date="2009-04-07"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.3.2 mode:FullText source:HeaderRef result:HeaderRef" date="2010-03-09"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-09"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-16"></event></eventGroup><numberingGroup><numbering type="pageFirst">497</numbering><numbering type="pageLast">506</numbering></numberingGroup><correspondenceTo>Department of Chemistry, San José State University, One Washington Square, San José, CA 95192‐0101</correspondenceTo><linkGroup><link type="toTypesetVersion" href="file:CHIR.CHIR20628.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="4"></count><count type="tableTotal" number="3"></count><count type="referenceTotal" number="55"></count><count type="wordTotal" number="1177"></count></countGroup><titleGroup><title type="main" xml:lang="en">Importance of hydrogen‐bonding sites in the chiral recognition mechanism between racemic D<sub>3</sub> terbium(III) complexes and amino acids</title><title type="short" xml:lang="en">Chiral Recognition of Amino Acids Using CPL</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Ahmed</givenNames><familyName>Moussa</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Christine</givenNames><familyName>Pham</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Shruthi</givenNames><familyName>Bommireddy</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af1" corresponding="yes"><personName><givenNames>Gilles</givenNames><familyName>Muller</familyName></personName><contactDetails><email>gilles.muller@sjsu.edu</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="US" type="organization"><unparsedAffiliation>Department of Chemistry, San José State University, One Washington Square, San José, California</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">circularly polarized luminescence</keyword><keyword xml:id="kwd2">lanthanide</keyword><keyword xml:id="kwd3">chirality</keyword><keyword xml:id="kwd4">amino acid</keyword></keywordGroup><fundingInfo><fundingAgency>National Institute of Health Minority Biomedical Research Support</fundingAgency><fundingNumber>2 S06 GM008192‐24A1</fundingNumber></fundingInfo><fundingInfo><fundingAgency>Research Corporation Cottrell Science Award</fundingAgency><fundingNumber>CC6624</fundingNumber></fundingInfo><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>The perturbation of the racemic equilibrium of luminescent D<sub>3</sub> terbium(III) complexes with chelidamic acid (CDA), a hydroxylated derivative of 2,6‐pyridine‐dicarboxylic acid (DPA), by added chiral biomolecules such as <sc>L</sc>‐amino acids has been studied using circularly polarized luminescence and <sup>13</sup>C NMR spectroscopy. It is shown in this work that the chiral‐induced equilibrium shift of [Tb(CDA)<sub>3</sub>]<sup>6−</sup> by <sc>L</sc>‐amino acids (i.e. <sc>L</sc>‐proline or <sc>L</sc>‐arginine) was largely influenced by the hydrogen‐bonding networks formed between the ligand interface of racemic [Tb(CDA)<sub>3</sub>]<sup>6−</sup> and these added chiral agents. The capping of potential hydrogen‐bonding sites by acetylation in <sc>L</sc>‐proline led to a ∼100‐fold drop in the induced optical activity of the [Tb(CDA)<sub>3</sub>]<sup>6−</sup>:<i>N</i>‐acetyl‐<sc>L</sc>‐proline system. This result suggested that the hydrogen‐bonding networks serve as the basis for further noncovalent discriminatory interactions between racemic [Tb(CDA)<sub>3</sub>]<sup>6−</sup> and added <sc>L</sc>‐amino acids. Chirality, 2009. © 2008 Wiley‐Liss, Inc.</p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Importance of hydrogen‐bonding sites in the chiral recognition mechanism between racemic D3 terbium(III) complexes and amino acids</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Chiral Recognition of Amino Acids Using CPL</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Importance of hydrogen‐bonding sites in the chiral recognition mechanism between racemic D3 terbium(III) complexes and amino acids</title></titleInfo><name type="personal"><namePart type="given">Ahmed</namePart><namePart type="family">Moussa</namePart><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, California</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Christine</namePart><namePart type="family">Pham</namePart><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, California</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Shruthi</namePart><namePart type="family">Bommireddy</namePart><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, California</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Gilles</namePart><namePart type="family">Muller</namePart><affiliation>Department of Chemistry, San José State University, One Washington Square, San José, California</affiliation><affiliation>E-mail: gilles.muller@sjsu.edu</affiliation><affiliation>Correspondence address: Department of Chemistry, San José State University, One Washington Square, San José, CA 95192‐0101</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><place><placeTerm type="text">Hoboken</placeTerm></place><dateIssued encoding="w3cdtf">2009-05</dateIssued><dateCaptured encoding="w3cdtf">2008-02-28</dateCaptured><dateValid encoding="w3cdtf">2008-05-28</dateValid><copyrightDate encoding="w3cdtf">2009</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">4</extent><extent unit="tables">3</extent><extent unit="references">55</extent><extent unit="words">1177</extent></physicalDescription><abstract 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.</abstract><note type="funding">National Institute of Health Minority Biomedical Research Support - No. 2 S06 GM008192‐24A1; </note><note type="funding">Research Corporation Cottrell Science Award - No. CC6624; </note><subject lang="en"><genre>keywords</genre><topic>circularly polarized luminescence</topic><topic>lanthanide</topic><topic>chirality</topic><topic>amino acid</topic></subject><relatedItem type="host"><titleInfo><title>Chirality</title><subTitle>The Pharmacological, Biological, and Chemical Consequences of Molecular Asymmetry</subTitle></titleInfo><titleInfo type="abbreviated"><title>Chirality</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><subject><genre>article-category</genre><topic>Regular Article</topic></subject><identifier type="ISSN">0899-0042</identifier><identifier type="eISSN">1520-636X</identifier><identifier type="DOI">10.1002/(ISSN)1520-636X</identifier><identifier type="PublisherID">CHIR</identifier><part><date>2009</date><detail type="volume"><caption>vol.</caption><number>21</number></detail><detail type="issue"><caption>no.</caption><number>5</number></detail><extent unit="pages"><start>497</start><end>506</end><total>10</total></extent></part></relatedItem><identifier type="istex">0E84689966BCA756674BA0BDCF53826BC9F114B0</identifier><identifier type="ark">ark:/67375/WNG-4D4FFG2K-M</identifier><identifier type="DOI">10.1002/chir.20628</identifier><identifier type="ArticleID">CHIR20628</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2008 Wiley‐Liss, Inc.</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-L0C46X92-X">wiley</recordContentSource><recordOrigin>Wiley Subscription Services, Inc., A Wiley Company</recordOrigin></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/document/0E84689966BCA756674BA0BDCF53826BC9F114B0/metadata/json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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