ThuliumV1, Pmc, Corpus, bibRecord, 000232

Importance of Hydrogen-Bonding Sites in the Chiral Recognition Mechanism Between Racemic D3 Terbium(III) Complexes and Amino Acids

Identifieur interne : 000232 ( Pmc/Corpus ); précédent : 000231; suivant : 000233

Importance 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 Muller

Source :

Chirality [ 0899-0042 ] ; 2009.

RBID : PMC:2668746

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.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2668746

DOI: 10.1002/chir.20628
PubMed: 18698640
PubMed Central: 2668746

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PMC:2668746

Le document en format XML

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 Terbium(III) Complexes and Amino Acids</title>
<author><name sortKey="Moussa, Ahmed" sort="Moussa, Ahmed" uniqKey="Moussa A" first="Ahmed" last="Moussa">Ahmed Moussa</name>
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<author><name sortKey="Pham, Christine" sort="Pham, Christine" uniqKey="Pham C" first="Christine" last="Pham">Christine Pham</name>
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<author><name sortKey="Bommireddy, Shruthi" sort="Bommireddy, Shruthi" uniqKey="Bommireddy S" first="Shruthi" last="Bommireddy">Shruthi Bommireddy</name>
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 Terbium(III) Complexes and Amino Acids</title>
<author><name sortKey="Moussa, Ahmed" sort="Moussa, Ahmed" uniqKey="Moussa A" first="Ahmed" last="Moussa">Ahmed Moussa</name>
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<author><name sortKey="Pham, Christine" sort="Pham, Christine" uniqKey="Pham C" first="Christine" last="Pham">Christine Pham</name>
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<author><name sortKey="Bommireddy, Shruthi" sort="Bommireddy, Shruthi" uniqKey="Bommireddy S" first="Shruthi" last="Bommireddy">Shruthi Bommireddy</name>
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<series><title level="j">Chirality</title>
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<front><div type="abstract" xml:lang="en"><p id="P2">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>
:<italic>N</italic>
-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.</p>
</div>
</front>
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<pmc article-type="research-article" xml:lang="EN"><pmc-comment>The publisher of this article does not allow downloading of the full text in XML form.</pmc-comment>
  <pmc-dir>properties manuscript</pmc-dir>
  <front><journal-meta><journal-id journal-id-type="nlm-journal-id">8914261</journal-id>
<journal-id journal-id-type="pubmed-jr-id">1771</journal-id>
<journal-id journal-id-type="nlm-ta">Chirality</journal-id>
<journal-title>Chirality</journal-title>
<issn pub-type="ppub">0899-0042</issn>
<issn pub-type="epub">1520-636X</issn>
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<article-categories><subj-group subj-group-type="heading"><subject>Article</subject>
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<title-group><article-title>Importance of Hydrogen-Bonding Sites in the Chiral Recognition Mechanism Between Racemic D<sub>3</sub>
 Terbium(III) Complexes and Amino Acids</article-title>
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<contrib-group><contrib contrib-type="author"><name><surname>MOUSSA</surname>
<given-names>AHMED</given-names>
</name>
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<contrib contrib-type="author"><name><surname>PHAM</surname>
<given-names>CHRISTINE</given-names>
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<contrib contrib-type="author"><name><surname>BOMMIREDDY</surname>
<given-names>SHRUTHI</given-names>
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<contrib contrib-type="author"><name><surname>MULLER</surname>
<given-names>GILLES</given-names>
</name>
<xref ref-type="author-notes" rid="FN1">*</xref>
</contrib>
<aff id="A1">Department of Chemistry, San José State University, One Washington Square, San José, California</aff>
</contrib-group>
<author-notes><fn fn-type="corresp" id="FN1"><label>*</label>
<p id="P1">Correspondence to: Gilles Muller, Department of Chemistry, San José State University, One Washington Square, San José, CA 95192-0101. E-mail: <email>gilles.muller@sjsu.edu</email>
</p>
</fn>
</author-notes>
<pub-date pub-type="nihms-submitted"><day>9</day>
<month>1</month>
<year>2009</year>
</pub-date>
<pub-date pub-type="ppub"><month>5</month>
<year>2009</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>1</day>
<month>5</month>
<year>2010</year>
</pub-date>
<volume>21</volume>
<issue>5</issue>
<fpage>497</fpage>
<lpage>506</lpage>
<abstract><p id="P2">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>
:<italic>N</italic>
-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.</p>
</abstract>
<kwd-group><kwd>circularly polarized luminescence</kwd>
<kwd>lanthanide</kwd>
<kwd>chirality</kwd>
<kwd>amino acid</kwd>
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<contract-num rid="GM1">S06 GM008192-24A10033</contract-num>
<contract-sponsor id="GM1">National Institute of General Medical Sciences : NIGMS</contract-sponsor>
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</front>
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Importance of Hydrogen-Bonding Sites in the Chiral Recognition Mechanism Between Racemic D3 Terbium(III) Complexes and Amino Acids

Importance of Hydrogen-Bonding Sites in the Chiral Recognition Mechanism Between Racemic D3 Terbium(III) Complexes and Amino Acids

Source :

Abstract

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