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A new chiral lanthanide NMR probe for the determination of the enantiomeric purity of alpha-hydroxy acids and the absolute configuration of alpha-amino acids in water.

Dickins, R. S. and Badari, A. (2006) 'A new chiral lanthanide NMR probe for the determination of the enantiomeric purity of alpha-hydroxy acids and the absolute configuration of alpha-amino acids in water.', Dalton transactions. (25). pp. 3088-3096.

Abstract

A water-soluble, enantiopure lanthanide complex, SSS-[Ln(.)L(3)], has been assessed as an effective chiral derivatising agent for the determination of the enantiomeric purity of a-hydroxy acids in aqueous solution. The complex displays superior chemical shift non-equivalence (Delta Delta delta similar to 2-11 ppm) for the diastereomeric resonances of interest compared to lanthanide shift reagents reported in the literature (Delta Delta delta < 0.1 ppm, typically). H-1 NMR studies have also revealed that SSS-[Ln(.)L(3)] can be used to determine the absolute configuration of a-amino acids at physiological pH, in water. The ability of SSS-[Ln(.)L(3)] to signal anion binding and, in particular, to distinguish between diastereomers through optical techniques such as lanthanide luminescence and circular dichroism has also been assessed.

Item Type:Article
Additional Information:
Full text:Full text not available from this repository.
Publisher Web site:http://dx.doi.org/10.1039/b513814k
Record Created:03 May 2007
Last Modified:08 Apr 2009 16:30

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