Journal
CHIRALITY
Volume 21, Issue 5, Pages 497-506Publisher
WILEY-BLACKWELL
DOI: 10.1002/chir.20628
Keywords
circularly polarized luminescence; lanthanide; chirality; amino acid
Funding
- National Institute of Health Minority Biomedical Research Support [2 S06 GM008192-24A1]
- Research Corporation Cottrell Science Award [CC6624]
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The perturbation of the racemic equilibrium Of luminescent D-3 termbium(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 C-13 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 1 proline led to a similar to 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 21:497-506, 2009. (C) 2008 Wilev-Uss, Inc.
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