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 approximately 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.
journal_name
Chiralityjournal_title
Chiralityauthors
Moussa A,Pham C,Bommireddy S,Muller Gdoi
10.1002/chir.20628subject
Has Abstractpub_date
2009-05-01 00:00:00pages
497-506issue
5eissn
0899-0042issn
1520-636Xjournal_volume
21pub_type
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