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Structural and NMR investigations of the ternary adducts of twenty alpha-amino acids and selected dipeptides with a chiral, diaqua-ytterbium complex.

Dickins, R. S. and Batsanov, A. S. and Howard, J. A. K. and Parker, D. and Puschmann, H. and Salamano, S. (2004) 'Structural and NMR investigations of the ternary adducts of twenty alpha-amino acids and selected dipeptides with a chiral, diaqua-ytterbium complex.', Dalton transactions. (1). pp. 70-80.

Abstract

A detailed investigation of the nature of the binding of each of the 20 common alpha-amino acids and various selected dipeptides to a chiral, diaqua-ytterbium complex in aqueous solution has been carried out. Analysis of the dipolar H-1 NMR paramagnetic shifts suggests that the alpha-amino acids form a common chelated structure within a nine-coordinate mono-capped square antiprismatic coordination environment, with the amine N axially disposed. Crystal structures of nine chelated YbL1-amino acid adducts (Gly, Ala, Ser, Thr, Met) confirm this. The ternary complexes with dipeptides (e.g. Gly-Ala, Gly-Ser, Gly-Met, Gly-Asp, Gly-Asn, Gly-His, Ser-Met, Asp-Phe, His-Gly) also favour the terminal amine as the axial donor with the proximate amide group binding to generate a five-ring chelate. Evidence for chelation through side-chain functionality was found only in the case of N-terminal Asp. The chiral environment about the ytterbium ion upon amino acid binding has also been probed using near-IR circular dichroism spectroscopy.

Item Type:Article
Full text:Full text not available from this repository.
Publisher Web site:http://dx.doi.org/10.1039/b311791j
Record Created:15 May 2007
Last Modified:20 Nov 2014 10:56

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