Copper(II) diamino acid complexes: quantum chemical computations regarding diastereomeric effects on the energy of complexation.

Org Lett

Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands.

Published: August 2003

[reaction: see text] Quantum chemical calculations were used to rationalize the observed enantiodifferentiation in the complexation of alpha-amino acids to chiral Cu(II) complexes. Apart from Cu(II)[bond]pi interactions and steric repulsions between the anchoring cholesteryl-Glu moiety and an aromatic amino acid R group, hydrogen bonding also plays a role. In fact, in the case of tryptophan, C[double bond]O...H[bond]N hydrogen bonding between the glutamate moiety and the tryptophan N[bond]H group compensates for the loss of intramolecular hydrogen-bonding and diminished Cu(II)[bond]pi interactions.

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http://dx.doi.org/10.1021/ol0351807DOI Listing

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